Sodium borohydride → HCID 23354004, compound

Participants

Reaction Steps

To a suspension of 1.3 g of 8-acetyl-4,4a, 5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one in methanol was added 300 mg of sodium borohydride under ice-cooling and the mixture was stirred for 3 hours. The mixture was concentrated in vacuo until about a half volume of the methanol was evaporated and water was added, and then extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel (SiO2 :30 g) column using a mixed solvent of chloroform and methanol (98:2) as an eluent. The resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane to give 570 mg of 8-(1-hydroxyethyl)-4,4a,5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one as a pale yellow powder, melting at 129°-145° C.

Provenance & Evidence