Hydrazine → 5-Amino-N-methoxy-2-methylbenzenesulfonamide

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Reaction Steps

N-Methoxy-2-methyl-5-nitrobenzenesulfonamide (0.5 g, 2 mmol) was combined with 10% palladium on carbon (0.05 g), ethanol (10 mL), and hydrazine (1 mL) and heated at reflux for 18 h. The solution was filtered through celite, concentrated, and purified on silica gel with methanol in dichloromethane. Product was an off white solid (0.28 g, 1.3 mmoL). 1H NMR (300 MHz, d6-DMSO) δ10.3 (s, 1H), 7.11 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 6.7 (d, J=8.2 Hz, 1H), 5.37 (s, 2H), 3.57 (s, 3H), 2.38 (s, 3H).

Provenance & Evidence