Hydrochloric Acid → 2-(4-Acetamidobutyryl)-5-chlorohydrocinnamic acid

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Reaction Steps

500 ml of 2N hydrochloric acid are added to a solution of 103 g (0.35 mol) of 4-acetyl-11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione in 1 l of tetrahydrofuran and the mixture is stirred at room temperature overnight. The mixture is concentrated in a vacuum, treated with methylene chloride and extracted twice with 2N sodium hydroxide solution; the aqueous phase is then acidified with 6N hydrochloric acid and extracted with methylene chloride. Removal of the solvent by distillation in a vacuum and chromatography on silica gel with methylene chloride/methanol (20:1) yields 2-(4-acetamidobutyryl)-5-chlorohydrocinnamic acid with melting point 90°-92°.

Provenance & Evidence