Methyl 2-amino-4-chloro-5-nitrobenzoate → 4-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-nitro-benzoic acid methyl ester

HRID 1857620

Reaction equation

HRID 1857620 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH2:14].[CH3:16][C:17]1[CH:18]=[C:19]([CH2:24][C:25](Cl)=[O:26])[CH:20]=[C:21]([CH3:23])[CH:22]=1>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH:14][C:25](=[O:26])[CH2:24][C:19]1[CH:18]=[C:17]([CH3:16])[CH:22]=[C:21]([CH3:23])[CH:20]=1

Participants

3

Reactant 2

HCID 15895692Methyl 2-amino-4-chloro-5-nitrobenzoateHCID 15895699(3,5-Dimethylphenyl)acetyl chloride2×

Product 1

HCID 543134564-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-nitro-benzoic acid methyl esterYield 72.4%

Procedure

To a suspension of 2-amino-4-chloro-5-nitrobenzoic acid methyl ester (989 mg in 15 mL of dry 1,2-dichloroethane) was added a solution of (3,5-dimethylphenyl)acetyl chloride (860 mg in 5 mL dry 1,2-dichloroethane) and the mixture heated at reflux on an oil bath. After 18 hours, an additional portion of (3,5-dimethylphenyl)acetyl chloride (274 mg in 1.5 mL dry 1,2-dichloroethane) was added and the mixture heated at reflux for an additional 5 hours. At this time the reaction was cooled and the solvent removed in vacuo. Recrystallization of the crude product from methanol gave the title compound (1.17 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux on an oil bath
  3. temperaturethe mixture heated
  4. temperatureat reflux for an additional 5 hours
  5. temperatureAt this time the reaction was cooled
  6. customthe solvent removed in vacuo
  7. customRecrystallization of the crude product from methanol

Sources & evidence

ORD record
ord-2ccc997bc0b7430fa270dc5eb73ac91d
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Linked notes

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