2-Methyl-5-(3-nitrophenyl)-2H-tetrazole → 3-(2-Methyl-2H-tetrazol-5-yl)aniline

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Reaction Steps

2-Methyl-5-(3-nitrophenyl)tetrazole (2.30 g, 0.0112 mol) was hydrogenated at 20 psi in ethanol (50 ml) using 10% palladium on carbon (230 mg) for 15 min. The mixture was filtered then evaporated to dryness in vacuo to give the title compound (1.55 g, 79%) as a colourless solid. mp 97° C. Rf 0.40 in dichloromethane:methanol (5:1) on silica plates. 1H NMR (360 MHz, CDCl3) δ 3.80 (2H, brs), 4.38 (3H, s), 6.78 (1H, ddd, J=8, 2 and 2 Hz), 7.26 (1H, dd, J=8 and 8 Hz), 7.47 (1H, dd, J=2 and 2 Hz), 7.51 (1H, dd, J=8 and 2 Hz).

Provenance & Evidence