4-Amino-N-(2-methylphenyl)benzenesulfonamide → HCID 47062676, compound

Participants

Reaction Steps

4-Amino-N-o-tolyl-benzenesulfonamide (12a) (RK1-1-24) I To a solution of 4-Nitro-N-o-tolyl-benzenesulfonamide (11a) in 4.0 mL of a 1:1 MeOH/THF mixture, was added nickel chloride hexahydrate (163 mg, 0.68 mmol) at 0° C. under constant stirring. Sodium borohydrate (52 mg, 1.37 mmol) was added portion wise and the progress of the reaction monitored by TLC (60% hexanes/40% ethylacetate). The solvent was removed in vacuo and the remaining black solid was re-suspended in EtOAc and filtered using a pad of celite and washed with EtOAc until the filtrate, when visualized under UV light, showed no product. The solvent was removed under vacuum affording the title compound as an off-white solid (0.045 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.0 Hz, 1H), 7.05 (td, J=2.0, 2.4, 2.4 Hz, 1H), 7.01-6.95 (m, 2H), 6.50 (d, J=8.8 Hz, 2H), 6.35 (br s, 1H), 4.05 (br s, 2H), 1.95 (s, 3H).

Provenance & Evidence