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

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Reaktionsschritte

2520 mg (10.8 mmol) 1-(2-methoxy-4-nitro-phenyl)-4-methyl-1H-imidazole dissolved in ethanol (110 ml) was hydrated under an atmosphere of hydrogen at room temperature for 3½ hours in the presence of 252 mg of 10% palladium on charcoal. 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 with methylene chloride/methanol 19/1. The fraction containing the product was suspended in diethyl ether, stirred for 15 minutes, filtered and dried to yield 1719 mg (78%) 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine as a yellow solid. MS ISP (m/e): 204.3 (100) (M+H)+. 1H NMR (CDCl3, 250 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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