2-Methyl-5-nitrobenzofuran → 2-Methyl-5-benzofuranamine

Participants

Reaction Steps

To a solution of 2-methyl-5-nitro-benzofuran [19] (125 mg, 0.706 mmol) in methanol (20 mL) was added 5% palladium on carbon (20 mg) and the mixture was stirred under 1 atm H2 for 4 h. The mixture was filtered through celite and the filtrate evaporated. The residue was passed through a silica plug to afford 5-amino-2-methyl benzofuran as a red-brown oil (78 mg, 75%), single spot at Rf 0.45 (1:1 hexane:ethyl acetate). 1H NMR (CDCl3): δ 7.17 (1H, d, J=8.7 Hz), 6.75 (1H, d, J=2.5 Hz), 6.57 (1H, dd, J8.7, 2.5 Hz), 6.20 (1H, s), 3.53 (2H, s, NH2), 2.39 (3 H, s).

Provenance & Evidence