Dimethyl Sulfoxide → 6-Iodo-4-propyl-quinoline-3-carbonitrile

Participants

Reaction Steps

A mixture of 2-(3-cyano-6-iodo-quinolin-4-yl)-2-ethyl-malonic acid diethyl ester (example 71a, 250 mg, 0.54 mmol), lithium chloride (45 mg, 0.72 mmol), water (10 uL, 0.54 mmol), and dimethylsulfoxide (10 uL) was heated at 180 degrees for 1 hour. After cooling to the room temperature, the reaction was quenched with water, followed by addition of ethyl acetate. The insoluble material was removed by filtration through a plug of celit with ethyl acetate. The water layer was extracted with ethyl acetate two more times. The organic layers were combined, washed with brain, dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude product as dark viscous oil. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 10-20% ethyl acetate in hexane in 30 min) afforded 6-iodo-4-propyl-quinoline-3-carbonitrile (40 mg, 23%) as a solid. LC-MS m/e 323 (MH+).

Provenance & Evidence