(3-Bromophenyl)acetyl chloride → 2-[2-(3-Bromophenyl)-acetylamino]-4-chloro-5-nitrobenzoic acid methyl ester

HRID 1857613Notes

Reaction equation

HRID 1857613 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].[Br:16][C:17]1[CH:18]=[C:19]([CH2:23][C:24](Cl)=[O:25])[CH:20]=[CH:21][CH:22]=1>ClC(Cl)C>[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:24](=[O:25])[CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([Br:16])[CH:18]=1

Participants

4

Reactant 2

HCID 13486899(3-Bromophenyl)acetyl chlorideHCID 15895692Methyl 2-amino-4-chloro-5-nitrobenzoate

Product 1

HCID 537529782-[2-(3-Bromophenyl)-acetylamino]-4-chloro-5-nitrobenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of 2-amino-4-chloro-5-nitrobenzoic acid methyl ester (Example 9, 780 mg in 10 mL dichloroethane) was added a solution of (3-bromophenyl)acetyl chloride (prepared essentially as described in Example 9, 866 mg in 5 mL dichloroethane) and the mixture heated to reflux on an oil bath. After 18 hours, the reaction mixture was concentrated in vacuo and the title compound obtained by crystallization from methanol (1.18 g).

Workup

  1. customprepared essentially
  2. temperatureheated
  3. temperatureto reflux on an oil bath
  4. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e0de2d9d4b1944f3bfe09d5798f4fb36
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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