Benzocaine → Ethyl 4-amino-3-chlorobenzoate

Participants

Reaction Steps

To a solution of ethyl 4-aminobenzoate (16 g.) in dry acetonitrile (200 ml.) at 60° was added N-chlorosuccinimide (13.35 g.) over 30 minutes. When the exothermic reaction had subsided the mixture was heated to reflux for 4 hours. After cooling the acetonitrile was removed under vacuum and the residue dissolved in dichloromethane. This was washed with 5% sodium hydroxide solution (2×100 ml.), brine and the organic layer dried over anhydrous magnesium sulphate. Evaporation yielded a solid that was purified by column chromatography on silica eluting with 10% ether/hexane.

Provenance & Evidence