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

Participants

Reaction Conditions

Reaction Steps

In an autoclave a suspension of 5% palladium on activated carbon (0.6 g) in 94% aqueous ethanol (200 mL) is pre-hydrogenated. After that, 4-methyl-1-(3-nitro-5-trifluoromethyl-phenyl)-1H-imidazole (6.0 g, 22.1 mmol) is added, and the mixture is hydrogenated at 70° C. and 4 bar pressure for 3 hours. Thereafter, most of the starting material is converted. The suspension is filtered over filter aid. The obtained filtrate is slowly added to water (250 mL) of 0-5° C. The resulting mixture is concentrated to a weight of 270 g, stirred, cooled to 0° C. and further stirred for almost 3 hours. The formed solid is filtered, washed with water (20 mL) and dried at 50° C. under reduced pressure to afford 3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenylamine as an off-white solid. Yield: 85.8% (HPLC purity: 94 area %), Melting range: 123-124° C.

Provenance & Evidence