Ammonia → HCID 22117857, compound

Participants

Reaction Steps

A solution of 1.94 g of 5,5-dimethyl-1,3-cyclohexanedione and 1.5 ml of a 25% aqueous solution of ammonia in 10 ml of absolute ethanol was heated at reflux under an atmosphere of nitrogen for 2 hours. The mixture was cooled to room temperature and 1.588 g of 4-bromo-3-nitrobenzaldehyde were added. The mixture was then heated at reflux for a further 18 hours, cooled and filtered. The residue was washed with 25 ml of cold diethyl ether and crystallized from dimethylformamide/water to give 2.36 g of 9-(4-bromo-3-nitro-phenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione as a yellow crystalline solid of melting point >300° C.

Provenance & Evidence