Ammonia → 10-hydroxy-10,11-dihydro-5,10-imino-[5H]dibenzo (a,d) cycloheptene-11-one

Participants

Reaction Conditions

Reaction Steps

10 g of 5-bromo-10,11-dihydro-[5H]-dibenzo (a,d) cycloheptene-10,11-dione was added to 250 ml of ammonia cooled to -40° C and then stirred for 1 hour at -40° C. The ammonia was distilled off and after adding 100 ml of 5 N hydrochloric acid thereto, the mixture was heated at 60°-65° C for 30 minutes. The mixture was cooled, made alkaline with addition of 110 ml of ammonium hydroxide and extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was crystallized from ether, vacuum filtered and dried to obtain 7.4 g of 10-hydroxy-10,11-dihydro-5,10-imino-[5H]dibenzo (a,d) cycloheptene-11-one dl melting at 214° C.

Provenance & Evidence