Hydrochloric Acid → HCID 23324916, compound

Participants

Reaction Steps

A solution of 34.1 g of 3-(3,4-dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester and β-(3,4-dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester in 110 ml of 1 N aqueous sodium hydroxide solution is heated to 60° C. for four hours. Excess aqueous hydrochloric acid (1 N, 120 ml) is added and the solution concentrated under reduced pressure to give β-(3,4-dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid, and 3-(3,4-dichlorophenyl)-5-oxo-2-pyrrolidinepropanoic acid. The acids are dissolved in 100 ml of acetic anhydride, and the solution is heated to 90° C. The solution is filtered hot and the filtrate concentrated in vacuo. The oil is chromatographed on silica gel (200-400 mesh) (elution with chloroform) to give cis- and transdihydro-1-(3,4-dichlorophenyl)-1H-pyrrolizine-3,5(2H, 6H)-diones as a white solid with mp 161°-167° C.

Provenance & Evidence