Chloromethyl Methyl Ether → 7-(Methoxymethoxy)-8-nitroquinaldine

Participants

Reaction Steps

Referring to FIG. 20, triethylamine (174 μL, 1.695 mmol) was added to a solution of 5a (174 mg, 0.847 mmol) in dry THF (5 mL) under a nitrogen atmosphere. Chloromethyl methyl ether (128 μL, 1.695 mmol) was added to the mixture dropwise and the reaction was stirred for 1 h. The reaction was diluted with chloroform, washed with water followed by brine. The organic layer was dried over Na2SO4, and the solvent was evaporated to afford 8a (200 mg, 0.806 mmol, 95%) as a bright yellow solid: 1H NMR (CDCl3) δ 8.00 (1H, d, J=8.4 Hz), 7.81 (1H, d, J=9.2 Hz), 7.47 (1H, d, J=8.8 Hz), 7.26 (1H, d, J=8.4 Hz), 5.35 (2H, s), 3.52 (3H, s), 2.69 (3H, s); 13C NMR (CDCl3) δ 162.5, 148.3, 140.3, 137.7, 135.7, 130.3, 122.2, 122.2, 115.4, 95.3, 57.0, 25.9; FTIR (neat) 2955, 1626, 1525, 1508, 1377, 1247, 1226, 1193, 1153, 1065, 991, 924, 835, 806, 656 cm−1; MS (ESI) m/z calculated for (C12H12N2O4+H)+ 249, found 249; HRMS (ESI) m/z calculated for (C12H12N2O4+H)+ 249.0875, found 249.0871.

Provenance & Evidence