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+).

1. additionAfter the completion of the addition
2. customthe resulting reaction mixture
3. customThe reaction mixture was evaporated
4. additiondiluted with 50 mL ethyl acetate
5. washwashed with saturated aqueous NaHCO3 solution (25 mL)
6. dry with materialdried (Na2SO4)
7. customevaporated
8. customThe residue was purified by silica gel column chromatography

ORD record

ord-3abd7d41c1d54139bdbd40deb02e5640

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247420B2