Hydrochloric Acid → HCID 12668038, compound

Participants

Reaction Steps

A solution of 5 g. (0.0166 mole) of 7,8-dihydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine in 250 ml. of methanol was acidified with ethereal hydrogen chloride to yield the hydrochloride salt. The latter was dissolved in 300 ml. of methanol and 4.0 g. (0.0176 mole) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added portionwise under nitrogen and the mixture stirred at room temperature for 20 minutes. Ether was added to the reaction mixture and the solvents decanted to leave 3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-dione hydrochloride. This hydrochloride was dissolved in a minimum amount of methanol and then added to a methanolic hydrogen chloride solution, portionwise. The mixture was stirred at room temperature for 1 hour, the solvent was evaporated and the residue triturated with acetonitrile. The separated solid was purified via conversion to its free base to give 9-chloro-7,8-dihydroxy-3-methyl-6-phenylthio-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 173°-174° C.

Provenance & Evidence