Methyl 4-chloroanthranilate → 4-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

HRID 1857626

Reaction equation

HRID 1857626 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH2:11].[CH3:13][C:14]1[CH:15]=[C:16]([CH2:21][C:22](Cl)=[O:23])[CH:17]=[C:18]([CH3:20])[CH:19]=1>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH:11][C:22](=[O:23])[CH2:21][C:16]1[CH:15]=[C:14]([CH3:13])[CH:19]=[C:18]([CH3:20])[CH:17]=1

Participants

3

Reactant 2

HCID 80001Methyl 4-chloroanthranilateHCID 15895699(3,5-Dimethylphenyl)acetyl chloride

Product 1

HCID 544849894-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl esterYield 90.6%

Procedure

To a solution of (3,5-dimethylphenyl)acetyl chloride (2.58 g in 20 mL dry dichloroethane) was added 2.5 g 2-amino-4-chlorobenzoic acid methyl ester and the mixture heated to reflux on an oil bath. After 2 hours, the pot was cooled to room temperature and the solvent removed in vacuo. Recrystallization of the crude product from methanol gave the title compound (4.05 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. customthe solvent removed in vacuo
  4. customRecrystallization of the crude product from methanol

Sources & evidence

ORD record
ord-73d697ff42214d9db0de91482510aafd
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Linked notes

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