Acetic Acid → 3-[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3-hydroxypropionitrile

Participants

Reaction Steps

In a 50 mL-volume glass flask equipped with a stirrer and a thermometer were placed under argon atmosphere 0.20 g (0.68 mmol) of 2-cyclopropyl-4-(4-fluorophenyl)-quinoline-3-carbaldehyde, 2 mL of acetonitrile and 0.042 g (1.06 mmol) of sodium hydride (purity: 60w). The content was stirred at room temperature for 2 hours. The resulting mixture was chilled to 0° C. To the chilled mixture was added 0.08 mL (1.40 mmol) of acetic acid, and the mixture was stirred for 5 minutes at the same temperature. Subsequently, to the mixture was added 10 mL of chilled water, and the mixture was extracted with 20 mL of ethyl acetate which were previously chilled in an ice bath. The organic portion was washed successively with 5 mL of saturated aqueous sodium hydrogen carbonate solution and 5 mL of saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The organic portion was then filtered and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography [column Wakogel C-200, available from Wako Junyaku Co., Ltd., eluent: ethyl acetate/hexane (7/93→15/85, vol. ratio)] to give 0.17 g (yield 75%) of 3-[2-cyclopropyl-4-(4-fluoro-phenyl)quinolin-3-yl]-3-hydroxypropionitrile as white solid.

Provenance & Evidence