1,3-dimethyl-4-nitro-1H-pyrazole-5-carboxamide → 4-amino-1,3-dimethyl-1H-pyrazole-5-carboxamide

Participants

Reaction Steps

To a solution of 1,3-dimethyl-4-nitro-1H-pyrazole-5-carboxamide (730 mg, 3.96 mmol) in anhydrous ethanol (100 mL) and ethyl acetate (100 mL) was added 10 wt % Pd on carbon (100.0 mg). The reaction mixture was evacuated with vacuum and purged with H2 (3×), then stirred under H2 at 50 psi for 5 hours. The reaction mixture was then filtered through a pad of Celite®. The filtrate was concentrated in vacuo and the crude was purified by column chromotagraphy (Si-PPC, gradient 0 to 30% methanol in dichloromethane) to get the desired product (597.0 mg, 97.7%) as a solid. 1H NMR (DMSO-d6, 400 MHz) δ ppm 7.26 (br s, 2H), 4.03 (br s, 2H), 3.84 (s, 3H), 2.02 (s, 3H); LC-MS m/z (method A)=155.2 [M+H]+, RT=0.35 min.

Provenance & Evidence