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4389-45-1 Usage

Uses

Different sources of media describe the Uses of 4389-45-1 differently. You can refer to the following data:
1. 2-Amino-3-methylbenzoic acid is a metabolite of Lidocaine, an antiarrythmic drug that is used to treat patients with ventricular fibrillation. 2-Amino-3-methylbenzoic acid has potential herbicidal activity, and is also used as a reagent to synthesize Ropicavaine, a local anasthetic.
2. 2-Amino-3-methylbenzoic acid is a metabolite of Lidocaine (L397800), an antiarrythmic drug that is used to treat patients with ventricular fibrillation. 2-Amino-3-methylbenzoic acid has potential herbicidal activity, and is also used as a reagent to synthesize Ropicavaine (R675000), a local anasthetic.

Chemical Properties

pink to grey-brown crystalline powder

Check Digit Verification of cas no

The CAS Registry Mumber 4389-45-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,8 and 9 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4389-45:
(6*4)+(5*3)+(4*8)+(3*9)+(2*4)+(1*5)=111
111 % 10 = 1
So 4389-45-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO2/c1-5-3-2-4-6(7(5)9)8(10)11/h2-4H,9H2,1H3,(H,10,11)

4389-45-1 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (B24230)  2-Amino-3-methylbenzoic acid, 98%   

  • 4389-45-1

  • 1g

  • 199.0CNY

  • Detail
  • Alfa Aesar

  • (B24230)  2-Amino-3-methylbenzoic acid, 98%   

  • 4389-45-1

  • 5g

  • 517.0CNY

  • Detail
  • Aldrich

  • (A62205)  2-Amino-3-methylbenzoicacid  99%

  • 4389-45-1

  • A62205-5G

  • 438.75CNY

  • Detail
  • Aldrich

  • (A62205)  2-Amino-3-methylbenzoicacid  99%

  • 4389-45-1

  • A62205-25G

  • 1,705.86CNY

  • Detail

4389-45-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Methylanthranilic acid

1.2 Other means of identification

Product number -
Other names 2-Amino-3-methylbenzoic acid

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:4389-45-1 SDS

4389-45-1Synthetic route

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr;99%
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 25857.4 Torr;99%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr;99%
2-chloro-3-methylbenzoic acid
15068-35-6

2-chloro-3-methylbenzoic acid

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With ammonia; sodium carbonate; copper(l) chloride In dimethyl sulfoxide at 130 - 150℃; for 5h;93.1%
7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide90%
With potassium chloride; dihydrogen peroxide; sodium hydroxide In water at 0 - 20℃; for 2.25h;80%
60%
3-methyl-2-nitrobenzoyl chloride
50424-93-6

3-methyl-2-nitrobenzoyl chloride

methyl 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilate
83325-79-5

methyl 3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilate

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

methyl 3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilate
83334-85-4

methyl 3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilate

Conditions
ConditionsYield
With lithium hydroxide In water; benzeneA n/a
B 61%
8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione
857203-66-8

8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With potassium hydroxide
methanol
67-56-1

methanol

7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

A

methyl 2-amino-3-methylbenzoate
22223-49-0

methyl 2-amino-3-methylbenzoate

B

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium methylate 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;
7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

butan-1-ol
71-36-3

butan-1-ol

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

3-Methylanthranilsaeure-n-butylester
79101-84-1

3-Methylanthranilsaeure-n-butylester

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydride 1.) 0-10 deg C 2.) room temperature, 30 min; Yield given. Multistep reaction;
3-methyl-2-nitrobenzonitrile
1885-77-4

3-methyl-2-nitrobenzonitrile

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
(i) H2, Pd-C, (ii) aq. NaOH; Multistep reaction;
3-methyl-2-nitrobenzoyl chloride
50424-93-6

3-methyl-2-nitrobenzoyl chloride

3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilic acid
78877-00-6

3-methyl-N-methyl-N-(3-methyl-2-aminobenzoyl)anthranilic acid

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilic acid
83325-80-8

3-methyl-N-methyl-N-<3-methyl-N-(3-methyl-2-nitrobenzoyl)anthraniloyl>anthranilic acid

Conditions
ConditionsYield
With lithium hydroxide In water; benzene Title compound not separated from byproducts;
7-methyl-1H-indole-2,3-dione
1127-59-9

7-methyl-1H-indole-2,3-dione

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

alkali

alkali

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione
857203-66-8

8-methyl-3-o-tolyl-1H-quinazoline-2,4-dione

aqueous NaOH

aqueous NaOH

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

o-toluidine
95-53-4

o-toluidine

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

ammonia
7664-41-7

ammonia

iron(II) sulfate

iron(II) sulfate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

hydrogenchloride
7647-01-0

hydrogenchloride

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

tin

tin

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

ethanol
64-17-5

ethanol

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

zinc dust

zinc dust

alkali

alkali

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

hydrogenchloride
7647-01-0

hydrogenchloride

3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

tin

tin

A

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

B

o-toluidine
95-53-4

o-toluidine

3-methyl-2-nitrobenzonitrile
1885-77-4

3-methyl-2-nitrobenzonitrile

alcoholic ammonium sulfide

alcoholic ammonium sulfide

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
at 100℃; im Rohr;
(2-amino-3-methyl-phenyl)-glyoxylic acid
859770-30-2

(2-amino-3-methyl-phenyl)-glyoxylic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

diluted NaOH-solution

diluted NaOH-solution

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

(2-amino-3-methyl-phenyl)-glyoxylic acid
859770-30-2

(2-amino-3-methyl-phenyl)-glyoxylic acid

sodium perborate

sodium perborate

diluted NaOH-solution

diluted NaOH-solution

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

m-Toluic acid
99-04-7

m-Toluic acid

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / HNO3 / 1 h / -10 °C
2: 99 percent / H2 / Pd/C / ethanol / 20 °C / 760 Torr
View Scheme
Multi-step reaction with 2 steps
1: fuming nitric acid
2: tin; hydrochloric acid
View Scheme
Multi-step reaction with 2 steps
1: fuming nitric acid
2: tin; hydrochloric acid
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / -10 - -5 °C
2: palladium 10% on activated carbon; hydrogen / methanol
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / 1 h / -10 °C
2: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 50 °C
View Scheme
m-Toluic acid
99-04-7

m-Toluic acid

aqueous ammonium polysulfide

aqueous ammonium polysulfide

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 49 percent / fuming nitric acid / 1 h / -10 °C
2: 89 percent / tin, hydrochloric acid / ethanol / 1.5 h / 70 °C
View Scheme
2-(hydroxyimino)-N-(2-methylphenyl)acetamide
1132-03-2

2-(hydroxyimino)-N-(2-methylphenyl)acetamide

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86percent H2SO4 / 1) 55 deg C, 10 min, 2) 75 deg C, 30 min
2: H2O2, NaOH
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / 0.33 h / 80 °C
2: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sulfuric acid / 60 - 80 °C
2.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
2.2: pH 4
View Scheme
3-Methylbenzonitrile
620-22-4

3-Methylbenzonitrile

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: concentrated hydrochloric acid / im Druckrohr
2: fuming nitric acid
3: tin; hydrochloric acid
View Scheme
3-Methyl-2-nitrobenzenecarboxamide
60310-07-8

3-Methyl-2-nitrobenzenecarboxamide

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3
2: (i) H2, Pd-C, (ii) aq. NaOH
View Scheme
o-toluidine
95-53-4

o-toluidine

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium sulfate / water / 40 °C
1.2: Reflux
2.1: sulfuric acid / 0.33 h / 80 °C
3.1: dihydrogen peroxide; sodium hydroxide / water / 0 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium sulfate / water / 40 °C
1.2: 0.17 h / Reflux
2.1: sulfuric acid / 60 - 80 °C
3.1: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
3.2: pH 4
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 55 °C
2: sulfuric acid / neat (no solvent) / 55 - 80 °C
3: sodium hydroxide; dihydrogen peroxide; potassium chloride / water / 2.25 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium sulfate; hydrogenchloride; hydroxylamine hydrochloride / water / 0.17 h / Reflux
2: sulfuric acid / 0.83 h / 70 - 80 °C
3: dihydrogen peroxide; sodium hydroxide / water / 0.5 h / 0 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1: hydroxylamine hydrochloride; sodium sulfate; hydrogenchloride / water / 12 h / 55 °C / Inert atmosphere
2: sulfuric acid / 0.67 h / Heating; Inert atmosphere
3: dihydrogen peroxide; sodium hydroxide / water / 5.5 h / 80 °C / Inert atmosphere
View Scheme
3-methyl-DL-kynurenine
1446522-57-1

3-methyl-DL-kynurenine

A

L-alanin
56-41-7

L-alanin

B

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With Pseudomonas fluorescens kynureninase In aq. phosphate buffer at 37℃; pH=8; Kinetics; Enzymatic reaction;
ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate
582319-05-9

ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / water / 2 h / 55 - 60 °C
2: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice
3: hydrogenchloride / water / 4 h / Reflux
4: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction
View Scheme
ethyl 7-methylindole-3-(3-acetamido-3-carboethoxy)butanoate

ethyl 7-methylindole-3-(3-acetamido-3-carboethoxy)butanoate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice
2: hydrogenchloride / water / 4 h / Reflux
3: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction
View Scheme
ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(2-formamido-3-methylphenyl)pentanoate
1446522-63-9

ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(2-formamido-3-methylphenyl)pentanoate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 4 h / Reflux
2: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction
View Scheme
methyl 2-amino-3-methylbenzoate
22223-49-0

methyl 2-amino-3-methylbenzoate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; ethanol; water at 50℃; for 3h; Inert atmosphere;
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-3-methylbenzyl alcohol
57772-50-6

2-amino-3-methylbenzyl alcohol

Conditions
ConditionsYield
Stage #1: 3-methylantranilic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;
Stage #2: With water; sodium hydroxide In tetrahydrofuran
100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h;97%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-5-bromo-3-methylbenzoic acid
206548-13-2

2-amino-5-bromo-3-methylbenzoic acid

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1h;100%
With bromine; acetic acid at 20 - 25℃;97%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 70 - 80℃; for 0.5h;95.6%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

methyl iodide
74-88-4

methyl iodide

methyl 2-amino-3-methylbenzoate
22223-49-0

methyl 2-amino-3-methylbenzoate

Conditions
ConditionsYield
Stage #1: 3-methylantranilic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.666667h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;
100%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 18.5h;92%
Stage #1: 3-methylantranilic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide for 24h;
77%
Stage #1: 3-methylantranilic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 24h;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;
3-carboxyphthalic anhydride
3786-39-8

3-carboxyphthalic anhydride

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

Conditions
ConditionsYield
at 150℃; for 12h;100%
6-[(R)-5-(3-amino-propyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one
1221280-89-2

6-[(R)-5-(3-amino-propyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-4-methyl-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-yl]-propyl}-benzamide

2-amino-4-methyl-N-{3-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-yl]-propyl}-benzamide

Conditions
ConditionsYield
100%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-5-chloro-3-methylbenzoic acid
20776-67-4

2-amino-5-chloro-3-methylbenzoic acid

Conditions
ConditionsYield
With chlorine In 1,2-dichloro-ethane at 50℃; for 3h; Solvent;98.1%
With N-chloro-succinimide In N,N-dimethyl-formamide at 70 - 80℃; for 0.5h;97.8%
With N-chloro-succinimide In N,N-dimethyl-formamide at 75℃;91%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

2-<(2-carboxyphenyl)amino>-3-methylbenzoic acid
80841-45-8

2-<(2-carboxyphenyl)amino>-3-methylbenzoic acid

Conditions
ConditionsYield
With copper; potassium carbonate; copper(I) bromide In various solvent(s) at 160℃; for 0.5h;98%
piperidine
110-89-4

piperidine

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

(2-amino-3-methylphenyl)(piperidin-1-yl)methanone

(2-amino-3-methylphenyl)(piperidin-1-yl)methanone

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 16h;98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

4-Chlorophenylsulfonyl isocyanate
5769-15-3

4-Chlorophenylsulfonyl isocyanate

3-(4-chlorobenzenesulfonyl)-8-methyl-2,4(1H,3H)-quinazolinedione

3-(4-chlorobenzenesulfonyl)-8-methyl-2,4(1H,3H)-quinazolinedione

Conditions
ConditionsYield
98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

C17H15NO4
698393-13-4

C17H15NO4

Conditions
ConditionsYield
at 110℃; for 16h; Inert atmosphere; neat (no solvent);98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-3-methylbenzamide
1885-32-1

2-amino-3-methylbenzamide

Conditions
ConditionsYield
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere;
Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide
98%
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere;
Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 16h; Inert atmosphere;
98%
Stage #1: 3-methylantranilic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere;
Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide for 16h; Inert atmosphere;
98%
p-chlorophenyl isoselenocyanate
14223-48-4

p-chlorophenyl isoselenocyanate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-(4-chlorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

2-(4-chlorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃; for 4.5h;98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-5-iodo-3-methylbenzoic acid
108857-24-5

2-amino-5-iodo-3-methylbenzoic acid

Conditions
ConditionsYield
With dipotassium peroxodisulfate; iodine In tetrachloromethane at 77℃; for 6h;97.7%
With N-iodo-succinimide In N,N-dimethyl-formamide at 20 - 80℃; for 2h;97%
With N-iodo-succinimide In N,N-dimethyl-formamide at 75℃; for 1h; Inert atmosphere;96%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

6,6'-dimethyl-1,1'-biphenyl-2,2'-dicarboxylic acid
57024-47-2, 108146-85-6, 19634-85-6

6,6'-dimethyl-1,1'-biphenyl-2,2'-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: 3-methylantranilic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #2: With copper(I) In water
97%
With Cu(I)-salt; sodium nitrite78%
Stage #1: 3-methylantranilic acid With sodium hydroxide; sodium nitrite at 0℃; for 0.5h;
Stage #2: With hydroxyammonium sulfate; copper(II) sulfate In water
72%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

2′-iodo-[1,1′-biphenyl]-2-yl benzoate

2′-iodo-[1,1′-biphenyl]-2-yl benzoate

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; sodium carbonate In 1,4-dioxane at 95℃; for 17h; Molecular sieve; Green chemistry;97%
phosgene
75-44-5

phosgene

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

6-methylisatoic anhydride
66176-17-8

6-methylisatoic anhydride

Conditions
ConditionsYield
In 1,4-dioxane; benzene Ambient temperature;96%
With sodium hydrogencarbonate In toluene at 0 - 20℃; for 0.25h;86%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

α,α-diphenylsuccinic acid anhydride
14702-32-0

α,α-diphenylsuccinic acid anhydride

2-(2,5-dioxo-3,3-diphenylpyrrolidin-1-yl)-3-methylbenzoic acid
297757-12-1, 297757-33-6, 297757-34-7

2-(2,5-dioxo-3,3-diphenylpyrrolidin-1-yl)-3-methylbenzoic acid

Conditions
ConditionsYield
at 150℃; for 12h; Condensation;96%
at 150℃; neat (no solvent, solid phase);
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

formamidine acetic acid
3473-63-0

formamidine acetic acid

8-methyl-4-quinazolinone

8-methyl-4-quinazolinone

Conditions
ConditionsYield
In formamide at 160℃; for 12h;96%
With formamide at 160℃;96%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

1-fluoro-4-isoselenocyanatobenzene
154592-60-6

1-fluoro-4-isoselenocyanatobenzene

2-(4-fluorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

2-(4-fluorophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃; for 4.5h;96%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

2-cyclohexyl-8-methyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

2-cyclohexyl-8-methyl-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
With acetic acid In ethanol for 6h; Reflux;96%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

6-methylisatoic anhydride
66176-17-8

6-methylisatoic anhydride

Conditions
ConditionsYield
In 1,4-dioxane for 6.5h; Reflux;95%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane94%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane94%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

1,2-cis-cyclohexanedicarboxylic anhydride
13149-00-3

1,2-cis-cyclohexanedicarboxylic anhydride

C16H17NO4
1185155-84-3

C16H17NO4

Conditions
ConditionsYield
at 110℃; for 10h; Inert atmosphere; neat (no solvent);95%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

4-bromophenyl isoselenocyanate
147695-56-5

4-bromophenyl isoselenocyanate

2-(4-bromophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

2-(4-bromophenylamino)-8-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40℃; for 4.5h;95%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

2-amino-5-bromo-3-methylbenzoic acid hydrobromide

2-amino-5-bromo-3-methylbenzoic acid hydrobromide

Conditions
ConditionsYield
With bromine; acetic acid In dichloromethane at 20℃; for 1h;95%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

acetic anhydride
108-24-7

acetic anhydride

2-acetylamino-3-methylbenzoic acid
67081-69-0

2-acetylamino-3-methylbenzoic acid

Conditions
ConditionsYield
for 2h; Reflux;94%
for 2h; Heating;87%
for 1h; Acetylation; Heating;85%
at 60℃; Reflux;
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

6-methylisatoic anhydride
66176-17-8

6-methylisatoic anhydride

Conditions
ConditionsYield
With bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 16.5h;94%
Multi-step reaction with 2 steps
1: triethylamine; dmap / acetonitrile / 2 h / 20 °C
2: 2-chloro-1-methyl-pyridinium iodide / acetonitrile / 0.17 h / 20 °C
View Scheme
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

formamidine acetic acid
3473-63-0

formamidine acetic acid

8-methylquinazolin-4(3H)-one
19181-54-5

8-methylquinazolin-4(3H)-one

Conditions
ConditionsYield
at 180℃; for 3h;94%
4-pentynoic acid
6089-09-4

4-pentynoic acid

3-methylantranilic acid
4389-45-1

3-methylantranilic acid

3a,9-dimethyl-3,3a-dihydro-1H-benzo[d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione
1227624-59-0

3a,9-dimethyl-3,3a-dihydro-1H-benzo[d]pyrrolo[2,1-b][1,3]-oxazine-1,5(2H)-dione

Conditions
ConditionsYield
With Echavarren's catalyst In 1,1-dichloroethane at 120℃; for 12h; Sealed vial;93%

4389-45-1Relevant articles and documents

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Chai, Jianqi,Chen, Min,Jin, Fei,Kong, Xiangyi,Wang, Xiaobin,Xue, Wei,Yang, Chunlong

, (2021/08/03)

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

A TRANSITION METAL COMPLEX COMPOUND

-

Page/Page column 16, (2021/07/31)

The present invention relates to a transition metal complex (Z) (described herein), which is stable and can be effectively used as a catalyst in various chemical transformations such as to prepare chemical intermediates, agrochemical compounds as well as pharmaceutical compounds.

PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE

-

Page/Page column 9; 17-18, (2021/02/26)

The present invention relates to two novel, efficient and one-pot methods for synthesizing chlorantraniliprole. In the first scheme, Chlorantraniliprole is prepared by a novel telescopic process starting from 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid a key raw material-A (Key RM-A). In the second scheme, starting from Key RM-A, the process steps use of a novel variant of anthranilic acid (Methyl 2-amino-5-chloro-3-methylbenzoate), to get Chlorantraniliprole. Furthermore, the present invention also relates to the synthesis of key starting material for the synthesizing chlorantraniliprole in-situ. All the in-situ steps of the disclosed synthesis methods obtain good yield, without using any expensive reagent or base or harsh reaction conditions, which makes the process simple, environment friendly and more cost effective. With this process the production cost of chlorantraniliprole and its intermediates is substantially reduced; fewer by-products are formed during its synthesis and since it's a one-pot reaction, isolation and purification are easy to achieve.

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