Abstract
The procedure of the Friedel-Crafts acylation of acetanilide was simplified and the yield raised by preliminary heating of acetanilide and aluminium trichloride, cooling of this mixture, and addition of aryl chloride. Exchange of N-aryl groups occured in benzoylation and 36% of the product was found to be 4′-benzoylbenzanilide. Separation of two products was easily effected by the difference in the rate of their hydrolysis.
Nitration of the 4′-acylacetanilide formed by this reaction was extremely facile and the yield was good in benzophenone derivatives but that of the others failed with mixed acids. This was very difficult even with other reagents, the yield of the purified product being around 20% when using nitric acid and acetic anhydride, and around 40% when using copper nitrate and acetic anhydride.
