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

Participants

Reaction Steps

2-Methyl-5-(3-nitrophenyl)tetrazole (2.30 g) was hydrogenated at 20 psi in ethanol (50 ml) using 10% palladium on carbon (230 mg) for 15 minutes. The mixture was filtered then evaporated to dryness in vacuo to give the title compound as a colourless solid (1.55 g), mp 97° C. Rf 0.40 in dichloromethane/methanol (5:1) on silica plates. 1H NMR (360 MHz, CDCl3) δ3.80 (2H, broad resonance), 4.38 (3H, s), 6.78 (1H, ddd, J1 =J2 =8 Hz, J3 =8 Hz), 7.26 (1H, dd, J1 =J2 =8 Hz), 7.47 (1H, dd, J1 =J2 =2 Hz), 7.51 (1H, dd, J1 =2 Hz, J2 =8 Hz).

Provenance & Evidence