N-(2-nitrophenyl)methanesulfonamide → N-(2-aminophenyl)methanesulfonamide
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of N-(2-nitrophenyl)methanesulfonamide (800 mg, 3.70 mmol) in methanol (20 mL) was added palladium on carbon (10% by weight, 394 mg, 0.37 mmol). The vessel was purged with hydrogen and then stirred for 4 hours under 1 atm of hydrogen. The reaction was filtered, concentrated and purified by chromatography to provide N-(2-aminophenyl)methanesulfonamide (600 mg, 87% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.67 (bs, 1H), 7.05 (dd, J=7.8, 1.5 Hz, 1H), 6.98 (m, 1H), 6.73 (dd, J=7.8, 1.5 Hz, 1H), 6.54 (m, 1H), 5.11 (bs, 2H), 2.90 (s, 3H).