Sodium hydride → 2-Hydroxyquinoline

To a stirred suspension of sodium hydride (0.019 g, 0.0004 mol) in 5 mL of anhydrous THF was added a solution of 3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl methanesulfonate (40) (0.13 g, 0.0004 mol) in 5 mL THF at ice-bath temperature followed by 7-(hydroxymethyl)-3,4-dihydroquinolin-2(1H)-one (37) (0.07 g, 0.0004 mol) in 5 mL THF dropwise. After the completion of the addition, the resulting reaction mixture was allowed to warm up to room temperature and stirred at 50° C. for 6 h. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was evaporated, diluted with 50 mL ethyl acetate, washed with saturated aqueous NaHCO3 solution (25 mL) followed by brine (25 mL), dried (Na2SO4) and evaporated. The residue was purified by silica gel column chromatography using 0-100% gradient of hexane and ethyl acetate to give the pure compound 41. Colorless oil (0.1 g, 62%). 1H NMR (400 MHz, CDCl3): δ 1.88 (quintet, J=6.8 Hz, 2H); 2.50 (t, J=7.6 Hz, 2H); 2.59 (t, J=7.6 Hz, 2H); 2.66 (broad s, 4H); 2.84 (t, J=7.6 Hz, 2H); 3.06 (broad s, 4H); 3.83 (s, 3H); 3.98 (t, J=7.6 Hz, 2H); 4.63 (s, 2H); 6.82-6.84 (m, 2H); 6.88-6.99 (m, 4H); 7.08-7.10 (m, 2H). MS (ESI): m/z=410.5 (M+H+).