Methoxymethyl 3-nitrophenyl ether → 3-MethoxyMethoxy-phenylaMine

Participants

Reaction Conditions

Reaction Steps

A solution of 11 (5.68 g, 31 mmol) in 310 mL moist ether (8:2:1 Et2O/EtOH/H2O) was cooled to 0° C., and treated with freshly prepared Al—Hg (5.2 g Al, 217 mmol) in small 1×1 cm pieces. The reaction mixture was stirred vigorously for 0.5 h at 0° C., and 1 h at 25° C. The reaction mixture was filtered through Celite, and the Celite was washed thoroughly with Et2O (5×50 mL). The filtrate was washed with saturated aqueous NaCl (300 mL), dried (Na2SO4), and concentrated under reduced pressure to afford 12 (4.23 g, 89%) as a golden oil, which was immediately carried on to the next step without further purification. For 12: 1H NMR (CDCl3, 250 MHz) δ 7.05 (t, J=8.0 Hz, 1H), 6.38 (m, 3H), 5.12 (s, 2H), 3.70 (br s, 2H), 3.46 (s, 3H); 13C NMR (CDCl3, 250 MHz) δ 158.2, 147.7, 129.9, 108.7, 106.0, 102.9, 94.0, 55.7; IR (film) νmax 3452, 3367, 2955, 2900, 1623, 1601, 1494, 1287, 1147, 1074, 1009 cm−; FABHRMS (NBA/NaI) m/z 153.0786 (C8H11NO2 requires 153.0790).

Provenance & Evidence