1-(Methoxymethoxy)-3-nitrobenzene → 3-MethoxyMethoxy-phenylaMine

Temperature

0 °C

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) δ7.05 (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, 250MHz) 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−1; FABHRMS (NBA/NaI) m/z 153.0786 (C8H11NO2 requires 153.0790).

1. additiontreated with freshly prepared Al—Hg (5.2 g Al, 217 mmol) in small 1×1 cm pieces
2. custom1 h
3. customat 25° C
4. filtrationThe reaction mixture was filtered through Celite
5. washthe Celite was washed thoroughly with Et2O (5×50 mL)
6. washThe filtrate was washed with saturated aqueous NaCl (300 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure

ORD record

ord-c03149efcc7f4133b81b13e5d615a69e

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06262271B1