Welcome to LookChem.com Sign In|Join Free

CAS

  • or

42924-53-8

Post Buying Request

42924-53-8 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

42924-53-8 Usage

Description

Nabumetone is a non-acidic, nonsteroidal antiinflammatory agent formally related to naproxen. Its main circulating metabolite is 6-methoxy-2-naphthylacetic acid (α-nornaproxen). Administered once daily (Tsub>1/2 * 30 hrs), nabumetone is reported to be effective in the treatment of rheumatoid and osteoarthritis.

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 42924-53-8 differently. You can refer to the following data:
1. Anti-inflammatory. Antibacterial.
2. anesthetic (local)
3. Nabumetone is an anti-inflammatory and antibacterial agent (1). A non-steroidal anti-inflammatory prodrug used for treatment of inflammatory and degenerative rheumatic diseases.

Definition

ChEBI: A methyl ketone that is 2-butanone in which one of the methyl hydrogens at position 4 is replaced by a 6-methoxy-2-naphthyl group. A prodrug that is converted to the active metabolite, 6-methoxy-2-naphthylacetic acid, following oral administration. It is s own to have a slightly lower risk of gastrointestinal side effects than most other non-steroidal anti-inflammatory drugs.

Indications

Nabumetone (Relafen) is approved for rheumatoid arthritis, osteoarthritis, and pain management. Its long half-life allows for once-daily dosing. Although this drug is a weak inhibitor of COX, it is metabolized in the liver to 6-methoxy-2-naphthylacetic acid (6-MNA), a strong COX inhibitor that is chemically similar to naproxen. As with most NSAIDs, GI side effects are most commonly reported. The incidence of gastric ulceration is lower with nabumetone than with many other NSAIDs.This is due to its nature as a prodrug, not to COX-2 selectivity. Lower-bowel complaints, rashes, and CNS disturbances are common adverse effects.

Manufacturing Process

4-(5-Bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one50 grams (0.179 moles) of 2-acetyl-5-bromo-6-methoxynaphthalene and 200 ml of n-butyl acetate are placed in a flask equipped with refrigerator and stirrer and, under stirring and at the temperature of 15°C, 14.5 g (0.268 moles) of sodium methoxide are added. The temperature of the reaction mixture goes up to 25°C and is kept at this value for 30 minutes, then the mixture is warmed at 65°C for one hour, is added with 100 ml of water and is brought to pH 4 by adding a concentrated aqueous solution of hydrochloric acid. The reaction mixture is then cooled to 0°-5°C and kept at this temperature for one hour. The solid is filtered, abundantly washed with water on the filter, then washed with butyl acetate and dried in oven under vacuum obtaining 53 g of product with a yield equal to 92%.Example 1. 4-(6-Methoxy-2-naphthyl)butan-2-one48 grams (0.150 moles) of 4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut- 3-en-2-one, 6.1 g of sodium acetate hydrate containing 32.4% of water, equivalent to 0.050 moles of sodium acetate, 4 g of a 50% suspension in water of 10% palladium on carbon, equivalent to 0.0019 moles of palladium, and 500 ml of methanol are put in a hydrogenator. The hydrogenator is washed with nitrogen in order to eliminate the oxygen and then hydrogen is introduced at the pressure of 2 atmospheres. The temperature of reaction is kept at 40°C for a period of time of 6 hours, then the hydrogen is let off, the hydrogenator is washed with nitrogen and the reaction mixture is filtered to eliminate the catalyst. The solution is brought to pH 6 with a 5% aqueous solution of sodium hydroxide and concentrated under vacuum. The oily residue is dissolved into 130 ml of isopropanol and 30 ml of N,Ndimethylformamide and the solution is added with 45 ml of water and 17.6 g of sodium bisulfite obtaining a suspension that is stirred for one hour at 60°C, then is cooled to 5°C and is filtered. The obtained solid is washed with 75 ml of methanol, suspended in 200 ml of a 5% aqueous solution of sodium hydroxide and kept under stirring at room temperature for three hours. The suspension is then filtered, the solid is washed with water until neutrality and dried in oven under vacuum obtaining 18 g of product with a yield equal to 52.8%.Example 2. 4-(6-Methoxy-2-naphthy)butan-2-oneThe reaction described above is repeated with the sole changes of doubling the amount of sodium acetate hydrate containing 32.4% of water, 12.22 g equivalent to 0.100 moles of sodium acetate, and of lowering the hydrogenation time to five hours. In this way 22.5 g of product are obtained with a yield equal to 66%.Example 3. 4-(6-Methoxy-2-naphthyl)butan-2-oneThe reaction described in example 3 is repeated with the sole changes of nearly triplicating the amount of sodium acetate hydrate containing 32.4% of water, 17.60 g equivalent to 0.145 moles of sodium acetate, and of lowering the hydrogenation time to five hours. The oil obtained by evaporating the solvent at the end of the reaction is treated with 300 ml of toluene and 100 ml of water and after 15 minutes of stirring the two layers are separated. The aqueous phase is discarded while the organic phase is evaporated under vacuum at 70°C obtaining an oil that is dissolved into 100 ml of methanol. The solution is kept at 0°C for two hours and the precipitated solid is filtered, washed with 15 ml of methanol cooled to 0°C and dried in oven under vacuum. In this way 21.7 g of product are obtained. The methanolic filtrates from crystallization and washing are concentrated under vacuum to half volume so obtaining, after cooling to 0°C, the crystallization of other 4 g of product with an overall yield equal to 75.3%.

Brand name

Relafen (Smith-Kline Beecham);RELIFEX.

Therapeutic Function

Antiinflammatory

General Description

Nabumetone (Relafen), a nonacidic NSAID prodrug, isclassified as an arylacetic acid, because it undergoes rapidhepatic metabolism to its active metabolite, 6-methoxy-2-naphthylacetic acid. Similar to the other arylacetic aciddrugs, it is used in short- or long-term management of RAand OA. Being nonacidic, it does not produce significantprimary insult to the GI mucosa lining and also has no effecton prostaglandin synthesis in gastric mucosa, thus producingminimum secondary GI damage when comparedwith other conventional NSAIDs.

Pharmacokinetics

Nabumetone is absorbed primarily from the duodenum. Milk and food increase the rate of absorption and the bioavailability of the active metabolite. Plasma concentrations of unchanged drug are too low to be detected in most subjects after oral administration, so most pharmacokinetic studies have involved the disposition of the active metabolite. Pharmacokinetic properties are altered in elderly patients, with higher plasma levels of the active metabolite being noted. Nabumetone undergoes rapid and extensive metabolism in the liver, with a mean absolute bioavailability of the active metabolite of 38%. The metabolism of nabumetone is illustrated in Figure 36.15. The major, most active metabolite is 6MNA, but the initial alcohol metabolite, a minor product, and its esters also possess significant anti-inflammatory properties.

Clinical Use

Nabumetone is indicated for the acute and chronic treatment of the signs and symptoms of osteoarthritis and rheumatoid arthritis. The recommended starting dosage is 1,000 mg as a single dose with or without food. More symptomatic relief of severe or persistent symp-toms may be obtained at doses of 1,500 or 2,000 mg/day

Drug interactions

Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage). Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparin, dabigatran and edoxaban - avoid long term use with edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Metabolism

Nabumetone is rapidly metabolised in the liver to the main active metabolite 6-methoxy-2-naphthylacetic acid (6-MNA). The metabolite is a potent inhibitor of prostaglandin synthesis. Excretion of the metabolite is predominantly in the urine.

Check Digit Verification of cas no

The CAS Registry Mumber 42924-53-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,9,2 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 42924-53:
(7*4)+(6*2)+(5*9)+(4*2)+(3*4)+(2*5)+(1*3)=118
118 % 10 = 8
So 42924-53-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H16O3/c1-17-14-7-6-12-9-11(3-5-13(12)10-14)4-8-15(16)18-2/h3,5-7,9-10H,4,8H2,1-2H3

42924-53-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Sigma-Aldrich

  • (N0020000)  Nabumetone  European Pharmacopoeia (EP) Reference Standard

  • 42924-53-8

  • N0020000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (N6142)  Nabumetone  analytical standard

  • 42924-53-8

  • N6142-5G

  • 1,220.31CNY

  • Detail
  • Sigma-Aldrich

  • (N6142)  Nabumetone  analytical standard

  • 42924-53-8

  • N6142-10G

  • 2,033.46CNY

  • Detail
  • USP

  • (1449518)  Nabumetone  United States Pharmacopeia (USP) Reference Standard

  • 42924-53-8

  • 1449518-200MG

  • 4,588.74CNY

  • Detail

42924-53-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name nabumetone

1.2 Other means of identification

Product number -
Other names Dolsinal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:42924-53-8 SDS

42924-53-8Synthetic route

4-(2-methoxynaphthalene-6-yl)but-3-en-2-one
127053-22-9, 56600-90-9

4-(2-methoxynaphthalene-6-yl)but-3-en-2-one

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With hydrogen In toluene at 50℃; under 3750.38 Torr; for 1h; Catalytic behavior; Temperature; Pressure; Inert atmosphere; Schlenk technique; Autoclave;99%
With 1% Pd on activated carbon; hydrogen In water at 45℃; under 760.051 Torr; for 15h; Reagent/catalyst; Green chemistry; chemoselective reaction;95%
With hydrogen In N,N-dimethyl-formamide at 100℃;90%
methyl vinyl ketone
78-94-4

methyl vinyl ketone

tris(6-methoxy-2-naphthyl)stibine

tris(6-methoxy-2-naphthyl)stibine

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With palladium diacetate; silver(I) acetate; acetic acid at 25℃; for 24h;99%
4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one
73356-31-7

4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
palladium on charcoal catalyst In acetic acid93%
Multi-step reaction with 3 steps
1: acetic acid; hydrogen; palladium on activated charcoal / 20 °C
2: sulfuric acid
3: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon; sulfuric acid / ethyl acetate
2: sulfuric acid
3: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr
View Scheme
6-methoxynaphthalene-2-carbaldehyde
3453-33-6

6-methoxynaphthalene-2-carbaldehyde

acetone
67-64-1

acetone

A

C18H22O2

C18H22O2

B

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With hydrogen; Pd/Mg-Al hydrotalcite at 74.84℃; under 3750.38 Torr; for 1.25h;A 11 % Chromat.
B 89%
2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

methyl vinyl ketone
78-94-4

methyl vinyl ketone

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With tetrabutylammomium bromide; tetra-(n-butyl)ammonium iodide; nickel dibromide In pyridine; N,N-dimethyl-formamide at 70℃; Electrochemical reaction;85%
Stage #1: methyl vinyl ketone With [2,2]bipyridinyl; water; cobalt(II) bromide In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 2-Bromo-6-methoxynaphthalene With pyridine; trifluoroacetic acid; lithium bromide; zinc In N,N-dimethyl-formamide at 80℃; for 0.333333h;
50%
2-hydroxy-3-butene
598-32-3

2-hydroxy-3-butene

2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

A

nabumetone
42924-53-8

nabumetone

B

4-(6-methoxy-2-naphthyl)-3-butene-2-ol
127053-21-8

4-(6-methoxy-2-naphthyl)-3-butene-2-ol

Conditions
ConditionsYield
Stage #1: 2-hydroxy-3-butene With dicyclohexylmethylamine; tetrabutylammomium bromide In N,N-dimethyl acetamide; water at 20℃; for 0.25h; Heck reaction;
Stage #2: 2-Bromo-6-methoxynaphthalene; 4'-hydroxyacetophenone oxime palladacycle catalyst In N,N-dimethyl acetamide; water at 120℃; for 9h; Heck reaction; Further stages.;
A 82%
B n/a
With sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride In various solvent(s) at 140℃; for 5h; Yield given;A n/a
B 9%
4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With sodium hydroxide; sodium acetate; sodium acetate trihydrate; palladium In methanol; water; hydrogen; toluene79.7%
With sodium hydroxide; sodium acetate; sodium acetate trihydrate; palladium In methanol; water; hydrogen; toluene79.7%
sodium metabisulfite

sodium metabisulfite

4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With sodium hydroxide; sodium acetate; palladium In water; hydrogen; isopropyl alcohol; toluene78.5%
With sodium hydroxide; sodium acetate; palladium In water; hydrogen; isopropyl alcohol; toluene78.5%
With sodium hydroxide; sodium acetate; palladium In water; hydrogen; isopropyl alcohol; toluene74.8%
With sodium hydroxide; sodium acetate; palladium In water; hydrogen; isopropyl alcohol; toluene74.8%
2-hydroxy-3-butene
598-32-3

2-hydroxy-3-butene

2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium formate; sodium hydrogencarbonate; Pd-benzothiazole carbene at 130℃; for 3h; Heck reaction;75%
With tetrabutylammomium bromide; sodium hydrogencarbonate; palladium dichloride at 120℃; for 6h; Heck coupling;74%
Stage #1: 2-hydroxy-3-butene With dicyclohexylmethylamine; tetrabutylammomium bromide In N,N-dimethyl acetamide at 20℃; for 0.25h; Heck reaction;
Stage #2: 2-Bromo-6-methoxynaphthalene; 4'-hydroxyacetophenone oxime palladacycle catalyst In N,N-dimethyl acetamide at 120℃; for 24h; Heck reaction; Further stages.;
90 % Spectr.
With Fe3O4@chitosan nanoparticles/Pd In ethanol at 140℃; for 24h;
6-methoxynaphthalene-2-carbaldehyde
3453-33-6

6-methoxynaphthalene-2-carbaldehyde

acetone
67-64-1

acetone

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; carbon monoxide In neat (no solvent) at 200℃; for 72h; Temperature; Autoclave;75%
With hydrogen; magnesium oxide; palladium at 59.84℃; under 3750.38 Torr; for 1h;98 % Chromat.
6-methoxynaphthalene-2-carbaldehyde
3453-33-6

6-methoxynaphthalene-2-carbaldehyde

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
67%
Multi-step reaction with 2 steps
1: aq. NaOH
2: H2 / Pd-C / ethyl acetate
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 210 °C / Continuous flow
2: hydrogen / N,N-dimethyl-formamide / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 0.12 h / 70 °C / Microwave irradiation; Continuous flow
2: hydrogen / N,N-dimethyl-formamide / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 4 h
2: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr
View Scheme
4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one
73356-31-7

4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one

A

4-(6-methoxynaphthalen-2-yl)butan-2-ol
65726-24-1

4-(6-methoxynaphthalen-2-yl)butan-2-ol

B

nabumetone
42924-53-8

nabumetone

C

(±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone
220786-56-1, 98386-83-5

(±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone

Conditions
ConditionsYield
With sulfuric acid; palladium 10% on activated carbon; hydrogen In ethyl acetateA 5%
B 65%
C 5%
2-(2-iodoethyl)-6-methoxynaphthalene

2-(2-iodoethyl)-6-methoxynaphthalene

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

methyl iodide
74-88-4

methyl iodide

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With [2,2]bipyridinyl; chloro-trimethyl-silane; nickel(II) bromide 2-methoxyethyl ether complex; zinc In tetrahydrofuran; N,N-dimethyl acetamide at 40℃; for 1h; Sealed tube; Inert atmosphere;54%
sodium acetate monohydrate

sodium acetate monohydrate

4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

4-(5-bromo-6-methoxy-2-naphthyl)-4-hydroxybut-3-en-2-one

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With sodium hydroxide; sodium acetate; sodium hydrogensulfite; palladium In methanol; water; hydrogen; N,N-dimethyl-formamide; isopropyl alcohol52.8%
With sodium hydroxide; sodium acetate; sodium hydrogensulfite; palladium In methanol; water; hydrogen; N,N-dimethyl-formamide; isopropyl alcohol52.8%
methyl 3-(6-methoxynaphthalen-2-yl)propanoate
136579-95-8

methyl 3-(6-methoxynaphthalen-2-yl)propanoate

methyl magnesium iodide
917-64-6

methyl magnesium iodide

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
In tetrahydrofuran at -55℃;51%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

2-Methoxynaphthalen-6-propionitril
42924-52-7

2-Methoxynaphthalen-6-propionitril

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
In diethyl ether Heating;
ethyl 2-acetyl-3-(6-methoxy-2-naphthyl) propionate

ethyl 2-acetyl-3-(6-methoxy-2-naphthyl) propionate

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With potassium hydroxide In water for 6h; Heating;4 g
2-(Bromomethyl)-6-methoxynaphthalene
73022-40-9

2-(Bromomethyl)-6-methoxynaphthalene

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / acetone / 3 h / Heating
2: 4 g / KOH / H2O / 6 h / Heating
View Scheme
2-(2-bromoethyl)-6-methoxynaphthalene
42924-51-6

2-(2-bromoethyl)-6-methoxynaphthalene

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. ethanol / Heating
2: diethyl ether / Heating
View Scheme
2-<1-hydroxyethyl>-6-methoxynaphthalene
32725-05-6, 56523-40-1

2-<1-hydroxyethyl>-6-methoxynaphthalene

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: PBr3 / benzene / Heating
2: aq. ethanol / Heating
3: diethyl ether / Heating
View Scheme
Multi-step reaction with 2 steps
1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 20 °C
2: [2,2]bipyridinyl; nickel(II) bromide 2-methoxyethyl ether complex; zinc; chloro-trimethyl-silane / N,N-dimethyl acetamide; tetrahydrofuran / 1 h / 40 °C / Sealed tube; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: (2-(dimethylamino)-N-(quinolin-8-yl)acetamido)nickel(II) chloride; manganese / N,N-dimethyl-formamide / 16 h / 20 °C / Sealed tube
View Scheme
methyl 6-methoxy-2-naphthylacetate
23981-48-8

methyl 6-methoxy-2-naphthylacetate

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: LiAlH4 / diethyl ether / Heating
2: PBr3 / benzene / Heating
3: aq. ethanol / Heating
4: diethyl ether / Heating
View Scheme
2-hydroxy-3-butene
598-32-3

2-hydroxy-3-butene

2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

A

C15H16O2

C15H16O2

B

nabumetone
42924-53-8

nabumetone

C

3-(6-methoxy-2-naphthyl)-2-butanone
56600-77-2

3-(6-methoxy-2-naphthyl)-2-butanone

Conditions
ConditionsYield
Stage #1: 2-hydroxy-3-butene With dicyclohexylmethylamine; tetrabutylammomium bromide In N,N-dimethyl acetamide at 20℃; for 0.25h; Heck reaction;
Stage #2: 2-Bromo-6-methoxynaphthalene; Kaiser oxime-derived complex on resin base In N,N-dimethyl acetamide at 120℃; for 24h; Heck reaction; Further stages. Title compound not separated from byproducts.;
2-hydroxy-3-butene
598-32-3

2-hydroxy-3-butene

2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

A

nabumetone
42924-53-8

nabumetone

B

3-(6-methoxy-2-naphthyl)-2-butanone
56600-77-2

3-(6-methoxy-2-naphthyl)-2-butanone

Conditions
ConditionsYield
Stage #1: 2-hydroxy-3-butene With dicyclohexylmethylamine; tetrabutylammomium bromide In N,N-dimethyl acetamide at 20℃; for 0.25h; Heck reaction;
Stage #2: 2-Bromo-6-methoxynaphthalene; Kaiser oxime-derived complex on resin base In N,N-dimethyl acetamide at 120℃; for 14h; Heck reaction; Further stages. Title compound not separated from byproducts.;
ethyl-5-(6-methoxy-2-naphthyl)-β-keto-pentanoate
1250259-21-2

ethyl-5-(6-methoxy-2-naphthyl)-β-keto-pentanoate

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
With water; potassium hydroxide In ethanol Conversion of starting material;
β-naphthol
135-19-3

β-naphthol

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: acetic acid; bromine / 0.5 h / 30 - 35 °C
2.1: acetic acid; tin / 3 h / 100 - 120 °C
3.1: potassium carbonate / acetone; water / 4 h / 10 - 50 °C / Cooling
4.1: magnesium; iodine / tetrahydrofuran / 5 h / Reflux
4.2: 1.75 h / 10 - 90 °C
4.3: 1 h / 20 °C
5.1: sodium hydroxide / water / 4 h
6.1: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr
View Scheme
1,6-dibromo-2-naphthol
16239-18-2

1,6-dibromo-2-naphthol

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetic acid; tin / 3 h / 100 - 120 °C
2.1: potassium carbonate / acetone; water / 4 h / 10 - 50 °C / Cooling
3.1: magnesium; iodine / tetrahydrofuran / 5 h / Reflux
3.2: 1.75 h / 10 - 90 °C
3.3: 1 h / 20 °C
4.1: sodium hydroxide / water / 4 h
5.1: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr
View Scheme
6-bromo-naphthalen-2-ol
15231-91-1

6-bromo-naphthalen-2-ol

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetone; water / 4 h / 10 - 50 °C / Cooling
2.1: magnesium; iodine / tetrahydrofuran / 5 h / Reflux
2.2: 1.75 h / 10 - 90 °C
2.3: 1 h / 20 °C
3.1: sodium hydroxide / water / 4 h
4.1: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr
View Scheme
2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

nabumetone
42924-53-8

nabumetone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium; iodine / tetrahydrofuran / 5 h / Reflux
1.2: 1.75 h / 10 - 90 °C
1.3: 1 h / 20 °C
2.1: sodium hydroxide / water / 4 h
3.1: hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
1.2: 1.42 h / Inert atmosphere
2.1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 20 °C
3.1: [2,2]bipyridinyl; nickel(II) bromide 2-methoxyethyl ether complex; zinc; chloro-trimethyl-silane / N,N-dimethyl acetamide; tetrahydrofuran / 1 h / 40 °C / Sealed tube; Inert atmosphere
View Scheme
nabumetone
42924-53-8

nabumetone

C15H11(2)H5O2

C15H11(2)H5O2

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate; water-d2 In tetrahydrofuran at 100℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; regioselective reaction;99%
nabumetone
42924-53-8

nabumetone

4-(5-iodo-6-methoxynaphthalen-2-yl)butan-2-one
1225055-49-1

4-(5-iodo-6-methoxynaphthalen-2-yl)butan-2-one

Conditions
ConditionsYield
With indium(III) triflate; N-iodo-succinimide In acetonitrile at 23℃; for 8h; Inert atmosphere; Darkness;97%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

p-butoxybenzaldehyde
5736-88-9

p-butoxybenzaldehyde

1-(4-butoxyphenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1363178-37-3

1-(4-butoxyphenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; p-butoxybenzaldehyde In ethanol at 25℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 25℃; for 22h; pH=4 - 5; Mannich reaction;
97%
nabumetone
42924-53-8

nabumetone

4-(6-methoxynaphthalen-2-yl)butan-2-ol
65726-24-1

4-(6-methoxynaphthalen-2-yl)butan-2-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at -10 - 20℃; for 4h;95%
With sodium tetrahydroborate In ethanol
With sodium tetrahydroborate In ethanol at -10℃; for 3h; Inert atmosphere;
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 3h; Schlenk technique; Inert atmosphere;
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

5-(6-methoxynaphthalen-2-yl)-1-p-tolyl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1363178-36-2

5-(6-methoxynaphthalen-2-yl)-1-p-tolyl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; 4-methyl-benzaldehyde In ethanol at 20℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 20℃; for 26h; pH=4 - 5; Mannich reaction;
95%
nabumetone
42924-53-8

nabumetone

Nabumetone hydroxyimine
68427-21-4

Nabumetone hydroxyimine

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol Heating;94%
With hydroxylamine hydrochloride
nabumetone
42924-53-8

nabumetone

C15H19NO

C15H19NO

Conditions
ConditionsYield
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 120℃; for 24h; chemoselective reaction;91%
With ammonia; hydrogen In tetrahydrofuran at 120℃; for 15h;90%
With N,N'-bis(salicylidene)-1,2-phenylene-diaminocobalt(II); ammonia; hydrogen In tetrahydrofuran; water at 130℃; for 24h; Autoclave;82%
With ammonium hydroxide; hydrogen at 140℃; under 48754.9 Torr; for 20h;
nabumetone
42924-53-8

nabumetone

4-Diazo-2,6-dibromo-2,5-cyclohexadienone
38676-25-4

4-Diazo-2,6-dibromo-2,5-cyclohexadienone

4-(5-(3,5-dibromo-4-hydroxyphenyl)-6-methoxynaphthalen-2-yl)butan-2-one

4-(5-(3,5-dibromo-4-hydroxyphenyl)-6-methoxynaphthalen-2-yl)butan-2-one

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} at 20℃; for 16h; Inert atmosphere; Schlenk technique; Molecular sieve;91%
nabumetone
42924-53-8

nabumetone

2,6-dichloro-4-diazocyclohexa-2,5-dien-1-one
31862-15-4

2,6-dichloro-4-diazocyclohexa-2,5-dien-1-one

4-(5-(3,5-dichloro-4-hydroxyphenyl)-6-methoxynaphthalen-2-yl)butan-2-one

4-(5-(3,5-dichloro-4-hydroxyphenyl)-6-methoxynaphthalen-2-yl)butan-2-one

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} at 20℃; for 16h; Inert atmosphere; Schlenk technique; Molecular sieve;90%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1-(4-bromophenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1363178-35-1

1-(4-bromophenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; 4-bromo-benzaldehyde In ethanol at 25℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 25℃; for 24h; pH=4 - 5; Mannich reaction;
89%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

1-(3,4-dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1206182-19-5

1-(3,4-dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; 3,4-dichlorobenzaldehyde In ethanol at 30℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 30℃; for 29h; pH=4 - 5; Mannich reaction;
89%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

5-(6-methoxynaphthalen-2-yl)-1-m-tolyl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1206182-16-2

5-(6-methoxynaphthalen-2-yl)-1-m-tolyl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; m-tolyl aldehyde In ethanol at 31℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 31℃; for 23h; pH=4 - 5; Mannich reaction;
89%
nabumetone
42924-53-8

nabumetone

methyl 3-diazo-6-oxocyclohexa-1,4-diene-1-carboxylate

methyl 3-diazo-6-oxocyclohexa-1,4-diene-1-carboxylate

methyl 2-hydroxy-5-(2-methoxy-6-(3-oxobutyl)naphthalen-1-yl)benzoate

methyl 2-hydroxy-5-(2-methoxy-6-(3-oxobutyl)naphthalen-1-yl)benzoate

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In 1,2-dichloro-ethane at 50℃; for 16h; Inert atmosphere; Schlenk technique; Molecular sieve;89%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

1-(4-hydroxyphenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1363178-38-4

1-(4-hydroxyphenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; 4-hydroxy-benzaldehyde In ethanol at 20℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 20℃; for 25h; pH=3 - 4; Mannich reaction;
88%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

5-(6-methoxynaphthalen-2-yl)-1-(4-methoxyphenyl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1206182-20-8

5-(6-methoxynaphthalen-2-yl)-1-(4-methoxyphenyl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; 4-methoxy-benzaldehyde In ethanol at 32℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 32℃; for 28h; pH=3 - 4; Mannich reaction;
87%
nabumetone
42924-53-8

nabumetone

C15H19NO*(x)ClH

C15H19NO*(x)ClH

Conditions
ConditionsYield
Stage #1: nabumetone With ammonium hydroxide; hydrogen at 60℃; under 7500.75 Torr; for 20h; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
87%
triphenylmethyl alcohol
76-84-6

triphenylmethyl alcohol

nabumetone
42924-53-8

nabumetone

4-(6-methoxynaphthalen-2-yl)-2-phenylbutan-2-ol

4-(6-methoxynaphthalen-2-yl)-2-phenylbutan-2-ol

Conditions
ConditionsYield
Stage #1: triphenylmethyl alcohol; nabumetone With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium tert-butylate; C69H57N2O2(1+)*BF4(1-)*H(1+) In toluene at 125℃; for 24h; Sealed tube;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;
86%
nabumetone
42924-53-8

nabumetone

sulfamethoxazole
723-46-6

sulfamethoxazole

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

C32H30N4O7S

C32H30N4O7S

Conditions
ConditionsYield
With hydrogenchloride In ethanol; chloroform; water at 20 - 32℃; for 27h;85%
nabumetone
42924-53-8

nabumetone

benzaldehyde
100-52-7

benzaldehyde

(E)-5-(2-methoxynaphthyl)-1-phenylpenta-1-en-3-one

(E)-5-(2-methoxynaphthyl)-1-phenylpenta-1-en-3-one

Conditions
ConditionsYield
Stage #1: nabumetone With sodium hydroxide In methanol at 20℃; for 0.0833333h;
Stage #2: benzaldehyde In methanol at 20℃; for 16h;
82%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

nabumetone
42924-53-8

nabumetone

5-[3-(6-Methoxy-naphthalen-2-yl)-1-methyl-prop-(E)-ylidene]-thiazolidine-2,4-dione

5-[3-(6-Methoxy-naphthalen-2-yl)-1-methyl-prop-(E)-ylidene]-thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperidine; benzoic acid In toluene Heating;80%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

1-(3-fluorophenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1363178-31-7

1-(3-fluorophenyl)-5-(6-methoxynaphthalen-2-yl)-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; 3-Fluorobenzaldehyde In ethanol at 13℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 13℃; for 23h; pH=4 - 5; Mannich reaction;
80%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

nabumetone
42924-53-8

nabumetone

benzaldehyde
100-52-7

benzaldehyde

5-(6-methoxynaphthalen-2-yl)-1-phenyl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one
1236218-15-7

5-(6-methoxynaphthalen-2-yl)-1-phenyl-1-(4-(trifluoromethyl)phenylamino)pentan-3-one

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine; benzaldehyde In ethanol at 31℃; for 0.333333h; Mannich reaction;
Stage #2: nabumetone With hydrogenchloride In ethanol; chloroform; water at 31℃; for 25h; pH=4 - 5; Mannich reaction;
79%

42924-53-8Downstream Products

42924-53-8Relevant articles and documents

Magnetic Fe3O4@chitosan nanoparticle: Synthesis, characterization and application as catalyst carrier

He, Linghao,Yao, Lu,Liu, Fujun,Qin, Bing,Song, Rui,Huang, Wei

, p. 6348 - 6355 (2010)

A novel method was developed to prepare Fe3O4@CS beads with core-shell structure using a double-crosslinking process. Before the coating process, an unique crosslinking agent, glutaraldehyde (GA), was adsorbed onto the surface of Fe3O4 in advance, so the subsequent CS can uniformly coat around the magnetic core processed from the strong interaction between GA and CS, forming a perfect core-shell structure. The obtained Fe3O4@CS beads were followed by the Pd deposition through in-situ reduction method, and the prepared composite catalyst was applied exemplarily in synthesizing nabumetone to check its reusing property. The nanoparticles were characterized by transmission electron microscopy (TEM), X-ray powder diffraction (XRD), Fourier transformation infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), and the magnetic hysteresis loop determination method. This novel composite catalyst showed admirable potential in reusable catalysis. Copyright

A Low Rhodium Content Smart Catalyst for Hydrogenation and Hydroformylation Reactions

Paganelli, Stefano,Tassini, Riccardo,Rathod, Vikas D.,Onida, Barbara,Fiorilli, Sonia,Piccolo, Oreste

, p. 1508 - 1521 (2020/10/15)

Abstract: This paper describes the preparation, broad characterization and study of activity in hydrogenation and hydroformylation reactions of an easily produced 0.18% Rh/Al2O3. Analytical studies on fresh and recycled samples shed light on the smart properties of such catalyst. Results showed high activity as well as fine/excellent chemoselectivity or regioselectivity, characteristics that may suggest a wide range of applicability. Graphic Abstract: The low metal content catalyst 0.18% Rh/Al2O3 was very active in both hydrogenation and hydroformylation reactions so providing intermediates for valuable APIs, as Nabumetone and Eletriptan, and a fragrance with a fresh, green-floral smell, that recalls scent of lily of the valley.[Figure not available: see fulltext.]

Environmentally responsible, safe, and chemoselective catalytic hydrogenation of olefins: ppm level Pd catalysis in recyclable water at room temperature

Gallou, Fabrice,Gao, Eugene S.,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.

supporting information, p. 6055 - 6061 (2020/10/14)

Textbook catalytic hydrogenations are typically presented as reactions done in organic solvents and oftentimes under varying pressures of hydrogen using specialized equipment. Catalysts new and old are all used under similar conditions that no longer reflect the times. By definition, such reactions are both environmentally irresponsible and dangerous, especially at industrial scales. We now report on a general method for chemoselective and safe hydrogenation of olefins in water using ppm loadings of palladium from commercially available, inexpensive, and recyclable Pd/C, together with hydrogen gas utilized at 1 atmosphere. A variety of alkenes is amenable to reduction, including terminal, highly substituted internal, and variously conjugated arrays. In most cases, only 500 ppm of heterogeneous Pd/C is sufficient, enabled by micellar catalysis used in recyclable water at room temperature. Comparison with several newly introduced catalysts featuring base metals illustrates the superiority of chemistry in water.

From Alkyl Halides to Ketones: Nickel-Catalyzed Reductive Carbonylation Utilizing Ethyl Chloroformate as the Carbonyl Source

Shi, Renyi,Hu, Xile

supporting information, p. 7454 - 7458 (2019/04/30)

Ketones are an important class of molecules in synthetic and medicinal chemistry. Rapid and modular synthesis of ketones remains in high demand. Described here is a nickel-catalyzed three-component reductive carbonylation method for the synthesis of dialkyl ketones. A wide range of both symmetric and asymmetric dialkyl ketones can be accessed from alkyl halides and a safe CO source, ethyl chloroformate. The approach offers complementary substrate scope to existing carbonylation methods while avoiding the use of either toxic CO or metal carbonyl reagents.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 42924-53-8