Diethyl Ether → 2-(4-Morpholinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate (1 g) in 4(2-hydroxyethyl)-morpholine (10 ml) at room temperature was added p-toluene sulphonic acid (20 mg), and the reaction mixture was warmed to 80° C. for 3 hours. The cooled mixture was treated with diethylether (50 ml), the resulting precipitate collected and dissolved in methanol (10 ml) and treated with hydrogen chloride in ethylacetate (2 ml of 5M). The mixture was stirred for 30 minutes and the resulting precipitate collected and recrystallised from ethanol-water to give 2-(4-morpholinyl)ethyl 5,7-dichloro-4-oxo-1,4-dihydroquinoline-2-carboxylate hydrochloride (0.45 g), m.p. 233° C. (dec). δ (360 MHz, D2O) 3.35 (4H, bs, morpholinyl-3,5-H), 3.55 (2H, t, CH2N), 4.06 (4H, bs, morpholinyl-2,6-H), 4.85 (2H, t, CO2CH2), 6.73 (1H, s, 3-H), 7.25 (1H, d, 6-H) and 7.40 (1H, d, 8-H). (Found: C, 46.94; H, 4.23; N, 6.84, Cl, 25.92%. C16H16Cl2N2O4. HCl. 0.4H2O requires C, 46.73; H, 4.26; N, 6.81; Cl, 25.86%).

Provenance & Evidence