1-(2-methoxy-4-nitrophenyl)-4-methyl-1H-imidazole → 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

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1-(2-Methoxy-4-nitro-phenyl)-4-methyl-1H-imidazole (2520 mg, 10.8 mmol) dissolved in ethanol (110 mL) was stirred under an atmosphere of hydrogen at room temperature for 3½ hours in the presence of 10% palladium on charcoal (252 mg). The catalyst was filtered off and washed with ethanol. The solvent of the filtrate was evaporated under reduced pressure. The crude product was purified on silica gel using dichloromethane/methanol (19:1 v/v) as eluent. The fraction containing the product was suspended in diethyl ether, stirred for 15 minutes, filtered and dried to yield the title compound (1719 mg, 78%) as a yellow solid. MS ISP (m/e): 204.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.48 (s, 1H), 6.91 (d, 1H), 6.88 (s, 1H), 6.35 (s, 1H), 6.17 (d, 1H), 3.68 (s, 3H), 2.11 (s, 3H).

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