HCID 67168207, compound → HCID 67169234, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-methyl-4-(methylsulfonyl)-3-nitrobenzenesulfonamide (1.5 g, crude) in EtOH (20 mL) and saturated aqueous NH4Cl (20 mL) was treated with Zn dust (3.3. g, 51 mmol) and stirred at 50° C. overnight before being filtered (EtOAc wash). The filtrate was diluted with water and extracted with EtOAc. The organic extract was washed with water and brine, dried (MgSO4), concentrated, and subjected to flash chromatography (33% EtOAc-petroleum ether) to give 3-amino-N-methyl-4-(methylsulfonyl)benzenesulfonamide (950 mg, 94% 2 steps) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73 (d, J=8.28 Hz, 1 H), 7.58 (q, J=4.94 Hz, 1 H), 7.34 (d, J=1.76 Hz, 1 H), 7.01 (dd, J=8.53, 1.76 Hz, 1 H), 6.48 (s, 2 H), 3.18 (s, 3 H), 2.47 (d, J=5.02 Hz, 3 H). MS (m/z) 265.0 (M+H+).

Provenance & Evidence