Benzocaine → p-(m-Bromobenzylidene)aminobenzoic acid ethyl ester

Participants

Reaction Steps

A mixture of 4-amino-benzoic acid ethyl ester (16.5 g, 100 mmol) and 3-bromo-benzaldehyde (18.5 g, 100 mmol) in ethanol (100 mL) was heated to reflux for 2 h. 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-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (20 g, 60%) as a white solid: LC/MS m/e calcd for C16H14BrNO2 M+: 332.2, observed: 332.0, 334.0.

Provenance & Evidence