3-Amino-5,5-dimethyl-2-cyclohexen-1-one → 9-(4-fluoro-3-chlorophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione

Participants

Reaction Steps

A solution of 1.39 g of 3-amino-5,5-dimethyl-2-cyclohexen-1-one and 793 mg of 4-fluoro-3-chlorobenzaldehyde in 10 ml of absolute ethanol and 1 ml of 1M aqueous hydrochloric acid was heated at reflux under a nitrogen atmosphere for 18 hours. The cooled mixture was filtered and the residue was washed with 25 ml of cold diethyl ether. Crystallization from absolute ethanol/water gave 302 mg of 9-(4-fluoro-3-chlorophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione as a pale yellow crystalline solid of melting point 274-275° C. (decomposition).

Provenance & Evidence