2-Methyl-5-(3-nitro-5-(trifluoromethyl)phenyl)-1,3,4-oxadiazole → 3-(5-Methyl-[1,3,4]oxadiazol-2-yl)-5-trifluoromethylphenylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-5-(3-nitro-5-(trifluoromethyl)phenyl)-1,3,4-oxadiazole (20 g, 73.2 mmol) and Pd/C (0.779 g, 7.32 mmol) in MeOH (25 mL) was stirred for 12 h at 35 psi under H2 atmosphere at 25° C. Then the mixture was filtered and the filtrate was concentrated to give the residue which was crystallized with MeOH (15 mL) to yield a gray solid of 3-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)aniline (17 g, 66.4 mmol, 91% yield): 1H NMR (400 MHz, CD3OD) δ 7.46 (s, 1H), 7.42 (s, 1H), 7.07 (s, 1H), 2.61 (s, 3H); ES-LCMS m/z 244 (M+H).

Provenance & Evidence