4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole → 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Participants

Reaction Steps

A suspension of 4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-imidazole (800 mg, 2.95 mmol) in MeOH (15 mL) was added to a solution of Pd/C (8.26 mg, 0.078 mmol) in MeOH (15 mL). The mixture was at 25° C. for 5 h under H2 atmosphere. Then the solution was concentrated and distributed between EA and saturated NaHCO3 solution. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by preparative HPLC (MeCN/H2O as eluants, basic condition) to yield a white solid of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (321.83 mg, 1.334 mmol, 86.0% yield). TLC (PE/EA=1:1, Rf=0.3): 1H NMR (400 MHz, CD3OD) δ 7.98 (s, 1H), 7.24 (s, 1H), 7.02-6.76 (m, 3H), 2.31-2.17 (m, 3H); ES-LCMS m/z 242.1 (M+H).

Provenance & Evidence