Water → HCID 18999061, compound

Participants

Reaction Steps

Pyridinium dichromate (18.7 g) was added to a stirred, cooled (0° C.) solution of (2-nitrophenyl)-(6-methoxypyridin-3-yl)methanol (2.0 g) in dimethylformamide (60 ml). After 2 hours at 0° C. water (100 ml) and ethyl acetate (50 ml) were added and the mixture allowed to warm to room temperature. The organic layer was separated and the aqueous extracted with ethyl acetate (3×100 ml). The combined organics were washed with water (2×100 ml) then brine (100 ml), dried (magnesium sulphate) then evaporated to dryness to give the title compound as a solid (1.90 g). mp 94°-95° C. Rf =0.35 in 33% ethyl acetate/petroleum ether (60-80) on silica plates; 1H NMR (360 MHz, CDCl3) δ 3.97 (3H, s), 6.63 (1H, d, J=9 Hz), 7.47 (1H, dd, J=1 and 8 Hz), 7.70 (1H, dd, J=8 Hz), 7.78 (1H, dd, J=8 Hz), 8.12 (1H, dd, J=3 and 9 Hz), 8.25 (1H, dd, J=1 and 8 Hz), 8.36 (1H, d, J=3 Hz); MS, m/z 258 for M+.

Provenance & Evidence