O-ethylhydroxylamine hydrochloride → N-[2-(3,5-dibromopyridin-2-yl)-2-(ethoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Participants

Reaction Steps

To 200 mg of N-[2-(3,5-dibromopyridine-2-yl)-2-oxoethyl]-2-(trifluoromethyl)benzamide in 1.4 ml of ethanol, 63 mg of ethoxyamine hydrochloride was added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, the resulting residue was mixed with 4 ml of water and extracted with ethyl acetate (4 ml×2), the resulting organic layers were combined, dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 5:95 to 50:50) as the eluent to obtain 195 mg of the desired product as a pale yellow resinous substance.

Provenance & Evidence