Diphenyl disulfide → 1-(4-Chlorophenyl)-5-methylisoquinoline

Participants

Reaction Steps

A mixture of 30 g of 1-(4-chlorophenyl)-5-methyl-3,4-dihydroisoquinoline and 30 g of diphenyl disulfide was dissolved in 800 ml of tetralin, and the solution was heated. After the reaction, the tetralin was distilled off under reduced pressure. The residue was dissolved in benzene, and extracted with a 2 N aqueous solution of hydrochloric acid. The aqueous layer was neutralized with an aqueous solution of sodium hydroxide, extracted with ether, and dried, followed by distilling off the solvent. Recrystallization of the residue from benzenecyclohexane afforded 18 g of 1-(4-chlorophenyl)-5-methylisoquinoline as colorless needles having a melting point of 122° to 123.5° C.

Provenance & Evidence