Hydrochloric Acid → N-acetylanthranilic acid

Participants

Reaction Steps

The isatoic anhydride and acetic anhydride were combined in a three necked, round bottomed flask equipped with a mechanical stirrer, dropping funnel, thermometer, reflux condenser and drying tube. The acetic anhydride was added to the mixture through the dropping funnel over a period of 30 minutes. The reaction was heated to 90°-100° C for 1.5 hours and then cooled to room temperature. The cooled reaction mixture was poured into a kilogram of ice containing 150 ml of concentrated hydrochloric acid. The white solid which precipitated was isolated, washed with 200 ml of water and dried to give 51.5 parts (94% yield) of N-acetylanthranilic acid having m.p. 183°-185° C.

Provenance & Evidence