Sodium borohydride → HCID 59396390, compound

Participants

Reaction Steps

Sodium borohydride (450 mg) was added with stirring to a solution of 6,8-dimethoxy-1-phenyl-3,4-dihydroisoquinoline (1.96 g) in EtOH (50 mL) over 5 minutes. The reaction mixture was stirred at room temperature for 2 hours and then further stirred at 60° C. for 1.5 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. An aqueous 3 M HCl solution (60 mL) was added to the resulting residue, followed by heating under reflux for 3 minutes. After cooling, an aqueous 20% NaOH solution was added to the mixture to have strong alkalinity, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to obtain 6,8-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (1.88 g).

Provenance & Evidence