Dipyridin-3-ylmethanone

614-18-6

35779-35-2

The general procedure for the synthesis of bis(pyridin-3-yl)methanone from ethyl nicotinate was as follows: n-butyllithium (n-BuLi) solution (71.3 mL, 1.6 M, 0.114 mol) was slowly added dropwise to an anhydrous ethyl ether (200 mL) solution of 3-bromopyridine (15 g, 0.095 mol) at -78 °C and the reaction was stirred for 15 min. Maintaining the temperature at -78 °C, a solution of anhydrous ethyl ether (50 mL) of ethyl acetate (13 g, 0.095 mol) was added dropwise to the above reaction mixture and stirring was continued at the same temperature for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate (NaHCO3) solution and subsequently treated with ammonium chloride (NH4Cl). Extraction was carried out with ethyl acetate and the organic layer was washed sequentially with saturated NaHCO3 solution and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated. The crude product was purified by neutral alumina column chromatography using methanol/dichloromethane as eluent to give bis(pyridin-3-yl)methanone (8.5 g, 49% yield) as a brown liquid.