Itaconic acid → 1-(4-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A 250 mL round-bottomed flask was charged with 4-fluoroaniline 50 (12.8 g, 115 mmol) and 2-methylenesuccinic acid 49 (15.0 g, 115 mmol). The flask was fitted with a reflux condenser then heated at 170° C. Once at that temperature, heating was continued for 15 min. After that time, the molten mass was cooled to room temperature and water was added. The resulting precipitate was filtered then dissolved in 2 N NaOH. The solution was filtered again and the filtrate was acidified using concentrated HCl. The resulting precipitate was collected by filtration and dried at 70° C. under vacuum to give 1-(4-fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid 51.

Provenance & Evidence