Anthranilic Acid → Bentranil

Participants

Reaction Steps

In a 500 ml three-necked flask provided with magnetic stirrer, reflux condenser, drying tube and dropping funnel, 2.81 g (20 mmol) of benzoyl chloride were dissolved in 50 ml of N,N-dimethylacetamide and 2.74 g (20 mmol) of 2-aminobenzoic acid as powder were added thereto while stirring. A mixture of 2.02 g (20 mmol) of triethylamine and 5 ml of N,N-dimethylacetamide were subsequently slowly added dropwise at room temperature. After stirring at room temperature for 1 hour, 200 ml of water were added and the precipitate formed was filtered off with suction, washed with water and dried at 80° C. under reduced pressure. The product was then heated in 50 ml of acetic anhydride under reflux for 2 hours. After cooling, the precipitate formed was filtered off with suction and washed with acetic acid and then with water. Recrystallization from n-hexane gave 3.65 g of product.

Provenance & Evidence