3-Bromobenzaldehyde → 2-[(3-Bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl ester

HRID 1801054

Reaction equation

HRID 1801054 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[NH2:11].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O>C(O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[N:11]=[CH:17][C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=1

Participants

4

Reactant 2

HCID 765833-BromobenzaldehydeHCID 78878Methyl 2-amino-5-chlorobenzoate

Product 1

HCID 674425752-[(3-Bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl esterYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-chloro-benzoic acid methyl ester (11.7 g, 63 mmol) and 3-bromo-benzaldehyde (11.7 g, 63 mmol) in ethanol (200 mL). The reaction mixture was heated to reflux for 2 hours. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 2-{[1-(3-bromo-phenyl)-methylidene]-amino}-5-chloro-benzoic acid methyl ester (5.3 g, 24%) as a white solid: LC/MS m/e calcd for C15H11BrClNO2 M+: 353.6, observed: 353.6.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-9197ae25f9ff49c49518f9379e22e07f
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Linked notes

Loading…