Potassium Hydroxide → 1-(2-Diethylaminoethyl)-3-hydroxy-3(2-chlorophenyl)-4-bromo-6-carbamoyloxindole

Participants

Reaction Steps

To 1-(2-diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-cyanooxindole (462.6 mg, 1.06 mmol) dissolved in anhydrous t-BuOH (30 mL) at 50° C. was added powdered KOH (1.2 g, 20 eq). The resulting solution was stirred for 1 hour and then cooled to room temperature. Ice was added and the mixture extracted with EtOAc (3×20 mL). The extracts were combined and dried (anhydrous MgSO4). After filtration, the solvent was removed in vacuo to give a light brown solid. Purification was carried out by column chromatography (silica gel, eluting EtOAc:EtOH:Et3N, 80:20:2) to yield the title compound as a white solid (346.5 mg, 69%).

Provenance & Evidence