Hydrochloric Acid → 5-(Pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one

Participants

Reaction Steps

A suspension of 5-chlorosulfonyl-2-oxindole (1.62 g, 7 mmol), pyrrolidine (0.701 mL, 8.4 mmol) and pyridine (1 mL) in dichloromethane (20 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and made acidic with 1 N hydrochloric acid (16 mL). The organic layer was then washed with sodium bicarbonate and brine, dried and concentrated. The residue was washed with ethanol (3 mL). It was then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9 to give 0.432 g (27%) 5-(pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one.

Provenance & Evidence