Hydrochloric Acid → 3-Chloro-4-nitroaniline

Participants

Reaction Steps

A mixture of N-(3-chloro-4-nitro-phenyl)-acetamide (18.55 g, 86.4 mmol) and an aqueous solution of hydrochloric acid (6 M, 120 mL) was heated at reflux for 2 hours. The resulting mixture was cooled and poured into water (800 mL); the yellow solid which crushed out was collected by filtration, washed with water and dried under reduced pressure to give 5 g of 3-chloro-4-nitro-phenylamine. The water layer was basified until pH 8 by addition of potassium carbonate and then was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 7.2 g of 3-chloro-4-nitro-phenylamine.

Provenance & Evidence