2-Nitrobenzaldehyde → HCID 18999062, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (6.7 ml of a 1.6M hexane solution) was added dropwise to a stirred, cooled (-100° C.) solution of 5-bromo-2-methoxypyridine (2.0 g, Eur. J. Med. Chem. 1977, 12, 531) in anhydrous tetrahydrofuran (60 ml), under a nitrogen atmosphere. After 20 minutes a solution of 2-nitrobenzaldehyde (1.61 g) in anhydrous tetrahydrofuran (30 ml)was added dropwise and the reaction mixture was stirred whilst maintaining the temperature between -90° and -100° C. for 2 hours. The reaction mixture was warmed to -85° C. then quenched with saturated aqueous ammonium chloride solution then 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 dried (magnesium sulphate) then evaporated to give a gum which was purified by column chromatography on silica using ethyl acetate/petroleum ether (60-80) (1:4) to afford an oil which solidified to give a low melting solid on standing (1.42 g). Rf =0.30 in 33% ethyl acetate/petroleum ether (60-80) on silica plates; 1H NMR (360 MHz, CDCl3) δ 2.60 (1H, broad s), 3.91 (3H, s), 6.43 (1H, s), 6.70 (1H, d, J=9 Hz), 7.48 (1H, dd, J=1 and 8 Hz), 7.53 (1H, dd, J=3 and 9 Hz), 7.67 (1H, dd, J=1 and 8 Hz), 7.83 (1H, d, J=8 Hz), 7.96 (1H, dd, J=1 and 8 Hz), 8.11 (1H, d, J=3 Hz); MS, m/z 261 for (M+H)+ ; IR (KBr) 3300 cm-1 (v. broad).

Provenance & Evidence