Phosphorus oxychloride → 1-chloro-7-methoxy-4-nitro-10H-acridin-9-one

Participants

Reaction Steps

A mixture of 12.9 g of 6-chloro-2[(4-methoxyphenyl)amino]-3-nitrobenzoic acid, 25 ml of chlorobenzene and 50 ml of phosphorus oxychloride was stirred and heated to reflux temperature over a period of one hour, and held under reflux for 4.5 hours. The mixture was cooled, filtered, and the filtrate concentrated to a viscous dark residue in vacuo. This residue and the precipitate collected previously were dissolved in 130 ml of acetic acid and cautiously treated with 15 ml of water with stirring. The resulting dark red solid was collected, washed with water, and dried to provide 11.5 g (95%) of the title compound, mp 262°-264° C.

Provenance & Evidence