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

HRID 1801104

Reaction equation

HRID 1801104 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>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[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

5

Reactant 2

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

Product 1

HCID 674425752-[(3-Bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl esterYield 99.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture solution of 2-amino-5-chloro-benzoic acid methyl ester (21 g, 113.2 mmol), 3-bromo-benzaldehyde (21 g, 113.2 mmol) and p-toluenesulfonic acid (431 mg, 2.2 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 2-[(3-bromo-benzylidene)-amino]-5-chloro-benzoic acid methyl ester (39.8 g, quant.) as a pale-white solid: MS calcd. for C15H11BrClNO2353.62, obsd. (ESI+) [(M+H)+] 351.9 & 353.9.

Workup

  1. temperatureto reflux for 12 hours
  2. customThe solvent was removed in vacuo
  3. washthe residue was washed with ether

Sources & evidence

ORD record
ord-72c0fc6a94444dd9b6ac73a96cdfaa85
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Linked notes

Loading…