1-methyl-5-(3-nitrophenyl)-1H-Tetrazole → 3-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)aniline

Participants

Reaction Steps

1-Methyl-5-(3-nitrophenyl)tetrazole (Example 13, 350 mg) was hydrogenated at 20 psi in ethanol (30 ml) using 10% palladium on carbon (35 mg) for 15 minutes. The mixture was filtered then evaporated to dryness in vacuo to give the title compound as a grey solid (220 mg), mp 156°-157° C. Rf 0.23 in dichloromethane/methanol (5:1) on silica plates. 1H NMR (360 MHz, CDCl3) δ3.92 (2H, broad resonance), 4.16 (3H, s), 6.86 (1H, ddd, J1 =J2 =2 Hz, J3 =8 Hz), 7.01 (1H, broad d, J=8 Hz), 7.06 (1H, dd, J1 =J2 =2 Hz), 7.32 (1H, dd, J1 =J2 =8 Hz).

Provenance & Evidence