Hydrochloric Acid → 3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile

Participants

Reaction Steps

In a 50 mL-volume glass flask equipped with a stirrer and a thermometer were placed under argon atmosphere 1.75 g (6.01 mmol) of 2-cyclopropyl-4-(4-fluorophenyl)-quinoline-3-carbaldehyde, 2.5 mL (47.5 mmol) of acetonitrile, 13.5 mL of methylal (dielectric constant at 20° C.: 2.7), and 0.56 g (10.3 mmol) of sodium methoxide. The content was reacted at 41° C. for 9 hours. The resulting mixture was chilled in an ice bath. To the chilled mixture were slowly added under stirring 30 mL of toluene and 7.0 mL (7.00 mmol) of hydrochloric acid (1 mol/L), successively. The separated organic portion was taken out. After washing with two portions of saturated aqueous sodium chloride solution (10 mL), the organic portion was dried over anhydrous magnesium sulfate. The organic portion was then filtered and analyzed by high performance liquid chromatography (absolute quantitative analysis). It was confirmed that 1.79 g (yield: 96%) of 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile was produced.

Provenance & Evidence