Sodium Hydroxide → HCID 131715104, compound

Participants

Reaction Steps

To 50 ml of tetrahydrofuran at -50° was added 2.7 g (0.02 mole) of anhydrous aluminum chloride. The slurry was added to a mixture of 2.2 g (0.058 mole) of lithium aluminum hydride in 100 ml of tetrahydrofuran at -30° and the mixture was stirred and allowed to warm to -20°. A solution of 5.6 g (0.0144 mole) of N-(6-methoxy-4-methyl-8-quinolinyl)-4-thiamorpholine-hexanamide in 50 ml of tetrahydrofuran was added to the mixture dropwise. The mixture was stirred at -10° for 3 hr, allowed to warm to room temperature and treated with 9.2 ml of 30% sodium hydroxide and 150 ml of water. The mixture was filtered through celite and concentrated to dryness in vacuo. The residual oil was chromatographed over 200 g of silica gel first with ethyl acetate and then with 2% methanol in ethyl acetate. The eluant containing product, Rf(silica gel--ethyl acetate)=0.17, was concentrated and the residual oil was taken up in 2-propanol and treated with excess of a saturated solution of hydrogen chloride in 2-propanol. The resulting precipitate was collected, washed with 2-propanol and dried in vacuo at 60° to afford 5.4 g (82%) of the title compound, mp 257°-259° (dec). The presence of 2-propanol was confirmed by NMR spectroscopy.

Provenance & Evidence