Water → HCID 18999059, compound

Participants

Reaction Steps

Cyclohexene (21 ml) was added to a stirred mixture of (2-nitrophenyl)-(5-bromo-2-methoxypyridin-4-yl)methanone (2.16 g) in ethanol (210 ml). A water slurry of 10% palladium on carbon (216 mg) was added followed by sodium acetate (524 mg). The suspension was heated to reflux for 4.5 hours then the mixture was cooled, filtered and evaporated to dryness. The residue was partitioned between dichloromethane and water. The organic layer was separated and the aqueous re-extracted with dichloromethane (twice). The combined organics were washed with water, brine, dried (sodium sulphate) then evaporated to dryness to give the title compound as a yellow solid (1.45 g). mp 82°-86° C. Rf =0.7 in 5% methanol/dichloromethane on silica plates; 1H NMR (360 MHz, CDCl3) δ 3.99 (3H, s), 6.57 (1H, ddd, J=1 and 7 Hz), 6.72 (1H, d, J=7 Hz), 6.86 (1H, s), 7.00 (1H, dd, J=1 and 5 Hz), 7.31 (1H, ddd, J=1 and 7 Hz), 7.37 (1H, dd, J=1 and 7 Hz), 8.26 (1H, d, J=5 Hz), IR (KBr) 3450, 3350, 1640 and 1620 cm-1.

Provenance & Evidence