Sodium borohydride → 7-(Methoxymethoxy)-8-nitroquinolin-2-yl methanol

Participants

Reaction Steps

Referring to FIG. 20, NaBH4 was added to a solution of 9a (18.1 mg, 0.0691 mmol) in absolute EtOH (5 mL). The reaction mixture was stirred for 15 min, diluted with chloroform, washed with water followed by brine. The organic layer was dried over Na2SO4 and the solvent was evaporated to afford 10a (8.3 mg, 0.032 mmol, 45%) as a yellow solid: 1H NMR (CDCl3) δ 8.14 (1H, d, J=8.8 Hz), 7.90 (1H, d, J=9.2 Hz), 7.58 (1H, d, J=9.2 Hz), 7.31 (1H, d, J=8.4 Hz), 5.39 (2H, s), 4.91 (2H, s), 3.54 (3H, s); 13C NMR (CDCl3) δ 162.4, 149.0, 139.1, 136.7, 131.9, 130.6, 123.1, 118.5, 116.3, 95.4, 64.5, 57.1; FTIR (neat) 3583, 2923, 1635, 1516, 1263, 1157, 1084, 1047, 931, 916, 804 cm−1; MS (ESI) m/z calculated for (C12H12N2O5+H)+ 265, found 265; HRMS (ESI) m/z calculated for (C12H12N2O5+H)+ 265.0824, found 265.0814.

Provenance & Evidence