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

HRID 1858062Notes

Reaction equation

HRID 1858062 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-0a55e9c5fc4046499b7ad5b86da0edc5
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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