Ammonium Hydroxide → 2-Oxoindoline-5-sulfonamide

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Reaction Steps

5-Chlorosulfonyl-2-oxindole (2.1 g) was added to 10 mL of ammonium hydroxide in 10 mL of ethanol and stirred at room temperature overnight. The mixture was concentrated and the solid collected by vacuum filtration to give 0.4 g (20% yield) of 5-aminosulfonyl-2-oxindole as an off-white solid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.67 (s, 1H, NH), 7.63–7.66 (m, 2H), 7.13 (s, 2H, 5-SO2NH2), 6.91 (d, 1H), 3.56 (s, 2H, CH2). MS m/z 211 [M−1]+.

Provenance & Evidence