4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole → 3-(Trifluoromethyl)-5-(4-methyl-1H-pyrazole-1-yl)aniline

Participants

Reaction Steps

To a solution of 4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole (560 mg, 2.065 mmol) in MeOH (10 mL) was added Pd/C (21.98 mg, 0.206 mmol) in one portion. Then the mixture was stirred under H2 for 12 h. LCMS analysis showed the starting material disappeared. The suspension was filtered through a pad of Celite® and the filter cake was washed with MeOH (2 mL). The combined filtrates were concentrated to dryness to give crude product, which was purified by preparative TLC (PE/EA=5/1, Rf=0.25) to afford pure product 3-(4-methyl-1H-pyrazol-1-yl)-5-(trifluoromethyl)aniline (280 mg, 1.158 mmol, 56.1% yield). 1H NMR (400 MHz, CD3OD): δ 7.96 (s, 1H), 7.52 (s, 1H), 7.15 (s, 2H), 6.82 (s, 1H), 2.15 (s, 3H). ES-LCMS: m/z 242.1 (M+H).

Provenance & Evidence