Ethanol → 6-(4-(2-Chloroethyl)phenyl)-pyridin-2-ylamine hydrochloride

Participants

Reaction Steps

To a 500 mL round-bottomed flask equipped with condenser and nitrogen inlet were added 9.0 g (29.0 mmol) 2-(2,5-dimethylpyrrol-1-yl)-6-(4-(2-chloroethyl)phenyl)-pyridine, 250 mL ethanol, 50 mL water, and 10.1 g (145 mmol) hydroxylamine hydrochloride. The reaction was refluxed for 36 hours, cooled, and the solvent was evaporated. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using 2% methanol in methylene chloride as eluant to afford 7.8 g (88%) of the product as a light brown solid.

Provenance & Evidence