Dimethylformamide → 4-[2-(3-Methoxyphenyl)-ethoxy]-quinoline-6-carbaldehyde

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Reaction Steps

To a solution of 2-(3-methoxyphenyl)-ethanol (359 mg, 2.36 mmol) in DMF (13 mL) was added sodium hydride (62.3 mg, 2.59 mmol) 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) (300 mg, 1.18 mmol) in DMF (3 mL) was added at 0° C. After addition, the reaction mixture was allowed to warm to room temperature and stirred for 30 min. During this period, the color of the solution was changed from white to black and then to brown. Then, the reaction mixture was heated to 60° C. and stirred for 15 h. After cooling to room temperature, 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 oily residue was dissolved in THF (3 mL) and 3 mL of HCl solution (3.0N) was added. The resulting solution was stirred for 2 h at room temperature. Then, it was neutralized with saturated sodium bicarbonate 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 residue was purified by using a Biotage silica gel column chromatography to obtain 133 mg (36.7% yield) of 4-[2-(3-methoxyphenyl)-ethoxy]-quinoline-6-carbaldehyde as a light yellow solid: EI-HRMS m/e calcd for C19H17NO3 (M+) 307.1208, found 307.1204.

Provenance & Evidence