Acetic Acid → 3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enal

Participants

Reaction Steps

In a 200 mL-volume glass flask equipped with a stirrer, a thermometer and a dropping funnel were placed under nitrogen atmosphere 4.0 g (12.7 mmol) of 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile (prepared in Reference Example 1), 1.6 g (25.4 mmol) of ammonium formate, 4.4 g (37.5 mmol as nickel atom) of water-containing developed Raney-nickel (NDHT-90, nickel content 50 wt. %, available from Kawaken Fine Chemical Co., Ltd.), and 40 mL of acetic acid. The content was reacted at 65° C. for 4 hours. After the reaction was complete, the content was cooled to room temperature. After addition of 20 mL of ethanol, the catalyst was removed by filtration using a celite. The filtrate was concentrated under reduced pressure, and 40 mL of ethyl acetate was added. The mixture was washed successively with 5 mL of hydrochloric acid (1 mol/L), 10 mL of water, 20 mL of aqueous sodium hydroxide solution (1 mol/L), 14 mL of an aqueous alkaline DL-tartaric acid solution (1.0 g of DL-tartaric acid was dissolved in 1 mol/L aqueous sodium hydroxide solution), and 20 mL of saturated aqueous sodium chloride solution. The organic portion was dried over anhydrous magnesium sulfate. The organic portion was filtered and concentrated under reduced pressure, to obtain 3.4 g (yield 82%) of 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enal as a pale yellow crystalline product (purity 98%, in terms of an area percent according to high performance liquid chromatography).

Provenance & Evidence