Benzocaine → 4-{[1-(3-Bromo-5-methyl-phenyl)-methylidene]-amino}-benzoic acid ethyl ester

Participants

Reaction Steps

A mixture of 4-amino-benzoic acid ethyl ester (8.3 g, 50.3 mmol) and 3-bromo-5-methyl-benzaldehyde (11.0 g, 50.3 mmol) in ethanol (100 mL) was prepared. 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 4-{[1-(3-bromo-5-methyl-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (7.3 g, 50%) as a white solid: LC/MS m/e calcd for C17H16BrNO2 M+: 346.2, observed: 346.1.

Provenance & Evidence