Ammonium formate → 2-Methoxy-4-phenylsulphonylaniline

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Reaction Steps

A solution of ammonium formate (0.1 83 g) in water (2.5 ml) was added to a mixture of 10% palladium on carbon (0.03 g) and 2-methoxy-4-phenylsulphonylnitrobenzene (Method 22) (0.213 g) in methanol (10 ml) and ethyl acetate (1 ml). The mixture was heated and stirred under reflux under argon for 4 hours then cooled and filtered through diatomaceous earth. The filter was washed with ethyl acetate (2×5 ml) and the filtrates were combined. The solution was concentrated by evaporation to approximately 2 ml and the resultant solid was collected, washed with water (2×5 ml) and dried in vacuo to give the title compound as a solid. M.p.149-150.5° C.; NMR: 3.8 (s, 3H), 5.78 (s, 2H), 6.67 (d, 1H), 7.17 (s, 1H), 7.26 (dd, 1H), 7.5-7.62 (m, 3H), 7.84 (d, 2H); MS: 262 (M−H)−; EA: C13H13NO3S requires C, 59.3; H, 5.0; N, 5.3; S, 12.2%; found: C, 59.1; H, 4.9; N, 5.2; S, 12.2%.

Provenance & Evidence