Ethyl Thioglycolate → HCID 70818364, compound

Participants

Reaction Steps

A solution of 6-bromoquinoline-5-carbonitrile (16b) (300 mg, 1.29 mmol), ethyl mercaptoacetate (212 μL, 1.93 mmol) and sodium ethoxide (122.6 mg, 1.80 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 15 hours. A saturated aqueous solution of sodium bicarbonate was added to the mixture. It was extracted twice with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The intermediate ethyl 2-[(5-cyanoquinolin-6-yl)sulfanyl]acetate obtained was reacted with sodium ethoxide (122.6 mg, 1.80 mmol) in dimethylformamide (8 mL) by stirring at 90° C. for 3 hours. The reaction was cooled to room temperature and water was added (10 mL). The resulting precipitate was filtered and washed with water twice and dried under vacuum with phosphorus pentoxide to afford the desired product (16c) as a solid (299 mg, 1.10 mmol, 85%).

Provenance & Evidence