Dimethylformamide → 4-(2-Dimethylamino-ethoxy)-quinoline-6-carbaldehyde

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Reaction Steps

To a solution of 2-dimethyamino-ethanol (500 mg, 5.61 mmol) in DMF (N,N-dimethylformamide) (30 mL) was added sodium hydride (161.5 mg, 6.73 mmol, 1.2 equiv.) at 0° C. and stirred for 15 min at this temperature. Then, a solution of butyl (4-chloroquinolin-6-ylmethylene)-amine (preparation was described in example 27b) (553.6 mg, 2.24 mmol) in DMF (5 mL) was added at 0° C. After addition, the reaction mixture was allowed to warm to room temperature and stirred for 15 h. Then, the mixture was diluted with saturated ammonium chloride solution and the organic compound was extracted into ethyl acetate (3×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solvent was removed under the vacuum and the brown residue was dissolved in THF (4 mL) and 6 mL of HCl solution (3.0N) was added. The resulting solution was stirred for 3 h at room temperature. Then, it was neutralized with sodium bicarbonate solution and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solvent was removed under the vacuum and the brown residue was purified by using a Biotage silica gel column chromatography to obtain 155 mg (11.3% yield) of 4-(2-dimethylamino-ethoxy)-quinoline-6-carbaldehyde as a brown solid: EI-HRMS m/e calcd for C14H16N2O2 (M+) 244.1212, found 244.1213.

Provenance & Evidence