Water → 4-(4-Bromo-imidazol-1-yl)-3-methoxy-phenylamine

Participants

Reaction Conditions

Reaction Steps

700 mg (2.35 mmol) 4-bromo-1-(2-methoxy-4-nitro-phenyl)-1H-imidazole and 2.755 g (12.2 mmol) stannous chloride dihydrate were suspended in a mixture of 40 ml ethyl acetate and 10 ml ethanol and stirred for 1 h at 70° C. The resulting mixture was poured into cold water and neutralized by addition of a saturated solution of sodium hydrogen carbonate. The product was extracted with ethyl acetate, dried and evaporated to give 627 mg (100%) of 4-(4-bromo-imidazol-1-yl)-3-methoxy-phenylamine as a yellowish solid. MS ISP (m/e): 268.0/270.1 (100/82) (M+H)+. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.49 (s, 1H), 7.77 (s, 1 H), 7.05 (s, 1H), 6.99 (d, 2H), 6.35-6.25 (m, 2H), 3.86 (s broad, 2H), 3.77 (s, 3H).

Provenance & Evidence