Methanol → Methyl 8-hydroxy-2-quinolinepropanoate

Participants

Reaction Steps

To a solution of (E)-3-[8-(benzyloxy)-2-quinolinyl]-2-propenoic acid (8d) (0.3 g, 0.98 mmol) in methanol (15 ml), 5% palladium on activated carbon (0.03 g) was added and the resulting suspension was hydrogenated by vigorous stirring for 2 hours at room temperature. The reaction mixture was filtered through a short column of silica gel (ca. 2 g) and the column was washed with methanol (10 ml). To the obtained filtrate, at room temperature, thionyl chloride (0.2 g, 1.7 mmol) was added with vigorous stirring. The reaction mixture was stirred overnight and then evaporated in vacuo. To the residue, a solution of 5% NaHCO3 (20 ml) was added and the mixture was extracted with ethyl acetate (50 ml). The extract was dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel with ether-petrol ether (1:2) as eluent to afford the title compound (0.158 g, 70%) as an oil. 1H NMR (CDCl3, HMDSO), δ: 2.89 (2H, t, J=7.0 Hz); 3.32 (2H, t, J=7.0 Hz); 3.65 (3H, s); 7.09 (1H, dd, J=2.0 and J=6.0 Hz); 7.16-7.49 (3H, m); 8.01 (1H, d, J=8.6 Hz).

Provenance & Evidence