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87-25-2

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87-25-2 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 87-25-2 differently. You can refer to the following data:
1. colourless liquid
2. Ethyl anthranilate has a faint, orange-flower odor and similar taste.

Occurrence

Reported found in grapes, orange juice, orange peel oil, starfruit and Vitis labrusca L.

Uses

Different sources of media describe the Uses of 87-25-2 differently. You can refer to the following data:
1. Ethyl 2-aminobenzoate is used as a reactant in the amination of aryl chlorides, bromides, and triflates.
2. Perfumery and flavors, similar to methyl anthranilate.

Preparation

By esterification of anthranilic acid with ethanol in the presence of acid catalysts; by reacting sodium hypochlorite with an alkaline solution of phthalimide

General Description

Colorless liquid with a fruity odor. Insoluble in water.

Air & Water Reactions

ETHYL ANTHRANILATE should be protected from air and light. Insoluble in water.

Reactivity Profile

ETHYL ANTHRANILATE may hydrolyze under acidic and basic conditions.

Fire Hazard

Flash point data for ETHYL ANTHRANILATE are not available. ETHYL ANTHRANILATE is probably combustible.

Pharmacology

Ethyl anthranilate behaved as a local anaesthetic, as measured by depression of muscle twitch, but was 50% less effective than the m- and p-aminobenzoate isomers. All three compounds potentiated the initial phase of caffeine-induced contracture of frog sartorius muscle, but the o-isomer had no effect on the peak tension of the contracture (Friedman, Bianchi & Weiss. 1974). It was proposed that the o-amino group has both steric and polar effects, its bulk preventing the inhibitory action of the carbonyl group on the caffeine-induced contracture of sartorius muscle, while the lone electron pair of the nitrogen atom induces a contracture on its own accord and potentiates a caffeine-induced contracture (Friedman, 1975). Ethyl anthranilate (0-1 mmol/litre) decreased the frequency of the electric-organ discharges of the electric fish, Gnathonemus moori, but did not affect the individual pulse amplitudes, indicating that the compound acted on the pacemaker cells of the mesencephalic command nucleus (Walsh & Schopp, 1966).

Safety Profile

Moderately toxic by ingestion. A skin irritant. Combustible liquid. When heated to decomposition it emits toxic fumes of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 87-25-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 87-25:
(4*8)+(3*7)+(2*2)+(1*5)=62
62 % 10 = 2
So 87-25-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H11NO2/c1-2-12-9(11)7-5-3-4-6-8(7)10/h3-6H,2,10H2,1H3

87-25-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A14378)  Ethyl anthranilate, 98+%   

  • 87-25-2

  • 50g

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (A14378)  Ethyl anthranilate, 98+%   

  • 87-25-2

  • 100g

  • 412.0CNY

  • Detail
  • Alfa Aesar

  • (A14378)  Ethyl anthranilate, 98+%   

  • 87-25-2

  • 250g

  • 940.0CNY

  • Detail
  • Alfa Aesar

  • (A14378)  Ethyl anthranilate, 98+%   

  • 87-25-2

  • 500g

  • 1275.0CNY

  • Detail

87-25-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ETHYL ANTHRANILATE

1.2 Other means of identification

Product number -
Other names Benzoic acid, 2-amino-, ethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:87-25-2 SDS

87-25-2Synthetic route

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

anthranilic acid
118-92-3

anthranilic acid

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
at 120℃; for 4h;98%
ethyl 2-nitrobenzoate
610-34-4

ethyl 2-nitrobenzoate

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With hydrogen; nickel In ethyl acetate at 30 - 35℃; under 760.051 Torr; for 10h;96%
With 6H(1+)*SiW12O40(6-)=H6[SiW12O40] In water at 20℃; for 18h; Inert atmosphere;96%
With 1,3-DIOXOLANE; water; zinc at 70℃; for 10h; Green chemistry; chemoselective reaction;87%
isatoic anhydride
118-48-9

isatoic anhydride

ethanol
64-17-5

ethanol

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With sodium hydride In mineral oil for 2h; Reflux; Inert atmosphere;89%
With sodium hydroxide at 65℃;72%
With sodium Heating;50.2%
With hydrogenchloride
2-Aminobenzyl alcohol
5344-90-1

2-Aminobenzyl alcohol

ethanol
64-17-5

ethanol

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With dihydrogen peroxide for 3h; Irradiation;82%
ethanol
64-17-5

ethanol

anthranilic acid
118-92-3

anthranilic acid

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With sulfuric acid Reflux;78.97%
Stage #1: ethanol; anthranilic acid With sulfuric acid In water for 20h; Heating / reflux;
Stage #2: With sodium hydroxide; water
78%
With thionyl chloride at 80℃; for 12h; Heating / reflux;61%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With potassium acetate; copper diacetate; palladium diacetate; potassium iodide In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 24h;78%
2-bromobenzoic acid ethyl ester
6091-64-1

2-bromobenzoic acid ethyl ester

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With copper (II)-fluoride; trimethylsilylazide; ethanolamine In N,N-dimethyl acetamide at 95℃; for 24h; Inert atmosphere;76%
With trimethylsilylazide; copper; ethanolamine In N,N-dimethyl acetamide at 95℃; for 24h; Inert atmosphere;55%
ethanol
64-17-5

ethanol

C8H6NO3(1-)*Na(1+)

C8H6NO3(1-)*Na(1+)

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With sodium hypochlorite In water at -10 - -8℃; for 0.666667h; Inert atmosphere;72.4%
ethanol
64-17-5

ethanol

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With dmap; ethyl 2-cyanoacetate at 20℃; for 4.5h; chemoselective reaction;72%
ethanol
64-17-5

ethanol

indole-2,3-dione
91-56-5

indole-2,3-dione

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With tert.-butylhydroperoxide; caesium carbonate at 20 - 30℃; for 4h; Sealed tube;72%
ethanol
64-17-5

ethanol

4-Octyne
1942-45-6

4-Octyne

carbon monoxide
201230-82-2

carbon monoxide

N-ethoxycarbonyl-2-iodoaniline
98952-64-8

N-ethoxycarbonyl-2-iodoaniline

A

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

B

3,4-dipropyl-2(1H)-quinolinone

3,4-dipropyl-2(1H)-quinolinone

Conditions
ConditionsYield
Stage #1: 4-Octyne; carbon monoxide; N-ethoxycarbonyl-2-iodoaniline With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 12h;
Stage #2: ethanol With sodium hydroxide at 20℃; for 0.5h;
A n/a
B 71%
2-(2-bromo-2-methyl-propionylamino)-benzoic acid ethyl ester

2-(2-bromo-2-methyl-propionylamino)-benzoic acid ethyl ester

A

ethyl 1,2,3,4-tetrahydro-3-methyl-2-oxoquinoline-8-carboxylate

ethyl 1,2,3,4-tetrahydro-3-methyl-2-oxoquinoline-8-carboxylate

B

ethyl 2-[(2-methyl-1-oxoprop-2-enyl)amino]benzoate
6607-32-5

ethyl 2-[(2-methyl-1-oxoprop-2-enyl)amino]benzoate

C

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
In acetonitrile at 20℃; for 5h; Irradiation;A 56%
B 11%
C n/a
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

(3,3-dimethyl-but-1-ynyl)benzene
4250-82-2

(3,3-dimethyl-but-1-ynyl)benzene

N-ethoxycarbonyl-2-iodoaniline
98952-64-8

N-ethoxycarbonyl-2-iodoaniline

A

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

B

3-tert-butyl-4-phenyl-2(1H)-quinolinone

3-tert-butyl-4-phenyl-2(1H)-quinolinone

Conditions
ConditionsYield
Stage #1: carbon monoxide; (3,3-dimethyl-but-1-ynyl)benzene; N-ethoxycarbonyl-2-iodoaniline With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 12h;
Stage #2: ethanol With sodium hydroxide at 20℃; for 0.5h;
A 39%
B 14%
ethanol
64-17-5

ethanol

4,4-dimethyl-2-pentyne
999-78-0

4,4-dimethyl-2-pentyne

carbon monoxide
201230-82-2

carbon monoxide

N-ethoxycarbonyl-2-iodoaniline
98952-64-8

N-ethoxycarbonyl-2-iodoaniline

A

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

B

3-tert-butyl-4-methyl-2(1H)-quinolinone

3-tert-butyl-4-methyl-2(1H)-quinolinone

Conditions
ConditionsYield
Stage #1: 4,4-dimethyl-2-pentyne; carbon monoxide; N-ethoxycarbonyl-2-iodoaniline With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 12h;
Stage #2: ethanol With sodium hydroxide at 20℃; for 0.5h;
A 30%
B 18%
(2,2-diethoxyvinylidene)triphenylphosphorane
21882-77-9, 53472-13-2

(2,2-diethoxyvinylidene)triphenylphosphorane

anthranilic acid
118-92-3

anthranilic acid

A

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

B

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
In tetrahydrofuran for 3h; Ambient temperature;A n/a
B 26%
phthalimide
136918-14-4

phthalimide

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With sodium hypochlorite; alkaline alcohol
isatoic anhydride
118-48-9

isatoic anhydride

ethanol
64-17-5

ethanol

A

2-((ethoxycarbonyl)amino)benzoic acid
41470-93-3

2-((ethoxycarbonyl)amino)benzoic acid

B

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
at 130 - 140℃; im Druckrohr;
2-amino-cyclohex-3-enecarboxylic acid ethyl ester
793634-65-8

2-amino-cyclohex-3-enecarboxylic acid ethyl ester

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl bromide
74-96-4

ethyl bromide

potassium anthranilate
37960-65-9

potassium anthranilate

A

ethyl 2-(ethylamino)benzoate
38446-21-8

ethyl 2-(ethylamino)benzoate

B

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With tetrabutylammomium bromide at 60℃; for 8h;A 10 % Chromat.
B 74 % Chromat.
With tetrabutylammomium bromide at 60℃; for 8h;A 20 % Chromat.
B 45 % Chromat.
diethyl sulfate
64-67-5

diethyl sulfate

potassium anthranilate
37960-65-9

potassium anthranilate

A

ethyl 2-(ethylamino)benzoate
38446-21-8

ethyl 2-(ethylamino)benzoate

B

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With tetrabutylammomium bromide at 60℃; for 2h;A 24 % Chromat.
B 63 % Chromat.
With tetrabutylammomium bromide at 60℃; for 2h;A 44 % Chromat.
B 46 % Chromat.
benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

A

3-aminobenzoic acid ethyl ester
582-33-2

3-aminobenzoic acid ethyl ester

B

p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

C

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With hydroxylamine-O-sulfonic acid; iron(II) sulfate In water; acetic acid at 40℃; for 2h; Yield given. Yields of byproduct given;
With hydroxylamine-O-sulfonic acid; iron(II) sulfate In water; acetic acid at 40℃; for 2h; Product distribution; Mechanism; k(C6H5COOEt)/k(C6H6);
N-carboethoxyaniline
101-99-5

N-carboethoxyaniline

A

aniline
62-53-3

aniline

B

p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

C

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
In cyclohexane Quantum yield; Mechanism; Irradiation;
ethanol
64-17-5

ethanol

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

hydrogenchloride
7647-01-0

hydrogenchloride

isatoic anhydride
118-48-9

isatoic anhydride

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

phthalimide
136918-14-4

phthalimide

sodium hypochlorite

sodium hypochlorite

alcoholic NaOH-solution

alcoholic NaOH-solution

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethanol
64-17-5

ethanol

hydrochloride of anthraniloyl chloride

hydrochloride of anthraniloyl chloride

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl iodide
75-03-6

ethyl iodide

anthranilate silver

anthranilate silver

A

2-(ethylamino)benzoic acid
89-50-9

2-(ethylamino)benzoic acid

B

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With toluene
ethanol
64-17-5

ethanol

ethyl 2-nitrobenzoate
610-34-4

ethyl 2-nitrobenzoate

Raney nickel

Raney nickel

hexachloroplatinum(IV)-acid

hexachloroplatinum(IV)-acid

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
Kinetics; Hydrogenation;
ethyl 2-nitrobenzoate
610-34-4

ethyl 2-nitrobenzoate

ammonium chloride

ammonium chloride

zinc dust

zinc dust

A

2,2'-azoxy-di-benzoic acid diethyl ester

2,2'-azoxy-di-benzoic acid diethyl ester

B

ethyl 2-(hydroxyamino)benzoate
38476-40-3

ethyl 2-(hydroxyamino)benzoate

C

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-nitrobenzyl chloride
610-14-0

2-nitrobenzyl chloride

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-(2-nitrobenzoylamino)-benzoate
326901-33-1

ethyl 2-(2-nitrobenzoylamino)-benzoate

Conditions
ConditionsYield
With pyridine In 1,2-dichloro-ethane at 20℃; for 0.75h; Inert atmosphere;100%
With sodium hydroxide
With benzene
With pyridine In 1,2-dichloro-ethane at 20℃; Inert atmosphere;
With pyridine In 1,2-dichloro-ethane at 20℃; for 0.75h; Inert atmosphere;2.24 g
1-Bromonaphthalene
90-11-9

1-Bromonaphthalene

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-(naphthalen-1-ylamino)benzoate

ethyl 2-(naphthalen-1-ylamino)benzoate

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80℃; for 17h; Buchwald-Hartwig Coupling; Inert atmosphere;100%
styrene
292638-84-7

styrene

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-[(1-phenylethyl)amino]benzoate

ethyl 2-[(1-phenylethyl)amino]benzoate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,4-dioxane at 100℃; for 24h;99%
benzyl chloroformate
501-53-1

benzyl chloroformate

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl N-benzyloxycarbonylanthranilate

ethyl N-benzyloxycarbonylanthranilate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 30℃; for 19h;98.6%
phthalic anhydride
85-44-9

phthalic anhydride

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-(2-ethoxycarbonylphenyl)phthalimide
120103-74-4

2-(2-ethoxycarbonylphenyl)phthalimide

Conditions
ConditionsYield
With triethylamine In toluene for 24h; Heating;98%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

4-quinolinic acid
486-74-8

4-quinolinic acid

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl (2-ethoxycarbonyl)phenylcarbamate
108890-73-9

ethyl (2-ethoxycarbonyl)phenylcarbamate

Conditions
ConditionsYield
With potassium carbonate In water; acetone98%
2,5-hexanedione
110-13-4

2,5-hexanedione

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-(2,5-dimethyl-1-pyrrol-1-yl)benzoate
928707-94-2

ethyl 2-(2,5-dimethyl-1-pyrrol-1-yl)benzoate

Conditions
ConditionsYield
In acetic acid for 1h; Paal-Knorr pyrrole synthesis; Inert atmosphere; Reflux;98%
2-Chloroanisole
766-51-8

2-Chloroanisole

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-((2-methoxyphenyl)amino)benzoate
23868-17-9

ethyl 2-((2-methoxyphenyl)amino)benzoate

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); biphenyl; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; tetrabutylammomium bromide; potassium hydroxide In water; ethyl acetate; toluene Inert atmosphere;98%
1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-(phenylamino)-3-(phenyl)-4(3H)-quinazolinone
4248-13-9

2-(phenylamino)-3-(phenyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 100℃; for 24h; Schlenk technique; Inert atmosphere;98%
With zinc trifluoromethanesulfonate In benzene at 80℃; for 8h;85%
(E)-N'-(2-cyano-5-(4-fluorophenyl)thiophen-3-yl)-N,N-dimethylformimidamide

(E)-N'-(2-cyano-5-(4-fluorophenyl)thiophen-3-yl)-N,N-dimethylformimidamide

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-(4-fluorophenyl)-7H-thiophene[3',2':4,5]pyrimidine[6,1-b]quinazolin-7-one

2-(4-fluorophenyl)-7H-thiophene[3',2':4,5]pyrimidine[6,1-b]quinazolin-7-one

Conditions
ConditionsYield
In acetic acid at 110℃; for 6h; Temperature; Concentration;98%
1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl N-(trimethylsilyl)anthranilate
130399-61-0

ethyl N-(trimethylsilyl)anthranilate

Conditions
ConditionsYield
With sulfuric acid for 0.5h; Heating;97%
1-chloro-3-methoxy-benzene
2845-89-8

1-chloro-3-methoxy-benzene

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-(3-methoxyphenylamino)benzoate
1028206-78-1

ethyl 2-(3-methoxyphenylamino)benzoate

Conditions
ConditionsYield
With potassium carbonate; XPhos palladium(II) phenethylamine chloride In tert-butyl alcohol at 110℃; for 0.5h;97%
diethyl malonate
105-53-3

diethyl malonate

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate
40059-53-8

ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

Conditions
ConditionsYield
With sodium In ethanol at 145℃; for 19h;96%
diethyl malonate
105-53-3

diethyl malonate

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

N,N'-di-2-carboethoxyanilide of malonic acid
100093-32-1

N,N'-di-2-carboethoxyanilide of malonic acid

Conditions
ConditionsYield
at 200 - 220℃; for 2h;96%
1-bromo-2-chloro-4-fluorobenzene
110407-59-5

1-bromo-2-chloro-4-fluorobenzene

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-((2-chloro-4-fluorophenyl)amino)benzoate
1331753-54-8

ethyl 2-((2-chloro-4-fluorophenyl)amino)benzoate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; potassium carbonate In tert-butyl alcohol at 100℃; for 5h; Inert atmosphere;96%
cyanoacetic acid
372-09-8

cyanoacetic acid

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-(2-cyanoacetamido)benzoate
904597-52-0

ethyl 2-(2-cyanoacetamido)benzoate

Conditions
ConditionsYield
Stage #1: cyanoacetic acid With phosphorus pentachloride In dichloromethane for 0.5h; Reflux;
Stage #2: 2-ethoxycarbonylaniline In dichloromethane for 2h; Reflux;
96%
diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

3-isopropyl-2-(isopropylamino)quinazolin-4(3H)-one
14333-75-6

3-isopropyl-2-(isopropylamino)quinazolin-4(3H)-one

Conditions
ConditionsYield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere;96%
With [(ImMesN)2Ti(NMe2)2] In neat (no solvent) at 60℃; for 12h; Mechanism; Solvent; Temperature; Reagent/catalyst; Glovebox; Schlenk technique;92%
With zinc trifluoromethanesulfonate In benzene at 80℃; for 8h;91%
3-iodobenzo[b]thiophene
36748-88-6

3-iodobenzo[b]thiophene

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-(3-benzothienylamino)benzoate

ethyl 2-(3-benzothienylamino)benzoate

Conditions
ConditionsYield
With copper; potassium carbonate In dibutyl ether for 24h; Reflux; Inert atmosphere;96%
succinic acid anhydride
108-30-5

succinic acid anhydride

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

4-[(2-ethoxycarbonylphenyl)amino]-4-oxobutanoic acid
120572-38-5

4-[(2-ethoxycarbonylphenyl)amino]-4-oxobutanoic acid

Conditions
ConditionsYield
In 1,4-dioxane; diethyl ether; benzene Ambient temperature;95%
In toluene at 20 - 115℃;
3-iodobenzonitrile
69113-59-3

3-iodobenzonitrile

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-[(3-cyanophenyl)amino]benzoate

ethyl 2-[(3-cyanophenyl)amino]benzoate

Conditions
ConditionsYield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene for 17h; Heating;95%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 17h; Heating;95%
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; tert-butyl alcohol at 100℃;91%
di-p-tolylcarbodiimide
726-42-1

di-p-tolylcarbodiimide

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-(p-tolyl)amino-3-(p-tolyl)-4(3H)-quinazolinone
125701-60-2

2-(p-tolyl)amino-3-(p-tolyl)-4(3H)-quinazolinone

Conditions
ConditionsYield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 100℃; for 24h; Schlenk technique; Inert atmosphere;95%
With zinc trifluoromethanesulfonate In benzene at 80℃; for 8h;89%
chloroacetonitrile
107-14-2

chloroacetonitrile

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-chloromethyl-1H-quinazolin-4-one

2-chloromethyl-1H-quinazolin-4-one

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 70℃;95%
4-Methoxyphenyl isocyanate
5416-93-3

4-Methoxyphenyl isocyanate

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

ethyl 2-(3-(4-methoxyphenyl)ureido)benzoate

ethyl 2-(3-(4-methoxyphenyl)ureido)benzoate

Conditions
ConditionsYield
With [(ImMesN)2Ti(NMe2)2] In neat (no solvent) at 20℃; for 12h; Glovebox; Schlenk technique;95%
ethyl chlorocarbonylacetate
36239-09-5

ethyl chlorocarbonylacetate

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-carboethoxymalonanilic acid ethyl ester
146828-48-0

2-carboethoxymalonanilic acid ethyl ester

Conditions
ConditionsYield
With pyridine In acetone for 5h; Ambient temperature;94%
With triethylamine In acetone Ambient temperature;94%
2,6-dimethylphenylisocyanate
28556-81-2

2,6-dimethylphenylisocyanate

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

methyl 2-(3-(2,6-dimethylphenyl)ureido)benzoate
204849-85-4

methyl 2-(3-(2,6-dimethylphenyl)ureido)benzoate

Conditions
ConditionsYield
In tetrahydrofuran for 24h; Ambient temperature;94%
pyridinium paratoluene sulfonic acid
84752-61-4

pyridinium paratoluene sulfonic acid

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-(3-nitrobenzenesulfonyl)benzoic acid ethyl ester

2-(3-nitrobenzenesulfonyl)benzoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: pyridinium paratoluene sulfonic acid With trifluoromethanesulfonic acid anhydride; Triphenylphosphine oxide In dichloromethane
Stage #2: 2-ethoxycarbonylaniline With triethylamine In dichloromethane at 0 - 20℃;
94%
chloroacetonitrile
107-14-2

chloroacetonitrile

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-(chloromethyl)quinazolin-4(3H)-one
3817-05-8

2-(chloromethyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
With hydrogenchloride In water for 0.5h; Microwave irradiation;94%
Stage #1: chloroacetonitrile; 2-ethoxycarbonylaniline With hydrogenchloride In 1,4-dioxane at 25℃; for 10.5h;
Stage #2: With ammonia In 1,4-dioxane; water at 0℃; pH=7;
81%
With hydrogenchloride In 1,4-dioxane for 6h; Cooling;
Stage #1: chloroacetonitrile; 2-ethoxycarbonylaniline With hydrogenchloride In 1,4-dioxane at 20℃; for 15h;
Stage #2: With sodium carbonate In 1,4-dioxane; water
benzonitrile
100-47-0

benzonitrile

2-ethoxycarbonylaniline
87-25-2

2-ethoxycarbonylaniline

2-phenyl-4(3H)-quinazolinone
1022-45-3

2-phenyl-4(3H)-quinazolinone

Conditions
ConditionsYield
Stage #1: benzonitrile; 2-ethoxycarbonylaniline at 25℃; for 0.166667h;
Stage #2: With hydrogenchloride at 25 - 80℃; for 4h;
94%

87-25-2Relevant articles and documents

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter

, p. 133 - 146 (2021/11/04)

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins

Qian, Peng,Liu, Jiaojiao,Zhang, Yan,Wang, Zhiyong

, p. 16008 - 16015 (2021/07/31)

A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.

PROCESS FOR THE PREPARATION OF QUINOLONE BASED COMPOUNDS

-

Paragraph 0288; 0290-0291, (2019/12/06)

The present invention relates to an improved process for the preparation of quinolone based compounds of general formula (I) using intermediate compound of general formula (XII). Invention also provides an improved process for the preparation of compound of formula (I-a) using intermediate compound of formula (XII-a) and some novel impurities generated during process. Compounds prepared using this process can be used to treat anemia.

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