Dichloromethane → N-(1,3,4,9-tetrahydro-7-hydroxy-2H-carbazol-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of 25.8 g (0.1 mol) of N-(1,3,4,9-tetrahydro-7-methoxy-2H-carbazol-2-yl)acetamide in 2 l. of CH2Cl2 was stirred at -50° to -60° C. under N2 while adding 101 g (0.4 mol) of BBr3 dropwise during 15-30 min. Stirring was continued for 30 min at -55° C. and then 3 hr at room temperature. After cooling to -40° C., 600 ml of MeOH was cautiously added dropwise during 45 min. The reaction mixture was allowed to warm to room temperature (ca. 1 hr) and then evaporated. The residue was dissolved in one l. of 1 N KOH, filtered from insolubles, and the cold filtrate was acidified (pH 3) with conc. HCl. The precipitate was filtered, washed with H2O, and recrystallized from i-PrOH to give the title compound, mp 245°-246°.

Provenance & Evidence