Ethanol → HCID 178422929, compound

Participants

Reaction Steps

To 570 mg. (14.2 mmoles) of potassium metal dissolved in 10 ml. of absolute ethanol was added a mixture of 4.33 g. (14.2 mmoles) of 2-methyl-4-acetylpyridine oxime tosylate in 20 ml. of absolute ethanol and the resulting mixture stirred at room temperature for 1.5 hours. The reaction was quenched with 100 ml. of ether and the potassium tosylate removed by filtration. Gaseous hydrogen chloride was bubbled into the filtrate for 5 minutes and the solution was concentrated. The residue was dissolved in 50 ml. of water and the solution was made basic with solid potassium carbonate. The aqueous was extracted with (5×20 ml.) chloroform and the combined organic extracts dried and concentrated to dryness giving an oil. The residual oil was dissolved in 25 ml. of methanol, 1.75 g. (14.2 mmoles) of ethyl acetimidate hydrochloride was added and the mixture was heated to reflux for 1.5 hours. The mixture was concentrated and the residue taken up in 25 ml. of concentrated hydrochloric acid. The acid solution was heated on a steam bath for one hour, then allowed to stir at room temperature for 18 hours. The mixture was made basic with solid potassium carbonate and was extracted with (2×50 ml.) chloroform and (1×50 ml.) ethyl acetate. The combined extracts were dried and evaporated leaving an oil which solidified on trituration with a toluene/cyclohexane/acetone mixture, 530 mg. (22%), m.p. 115°-117° C.

Provenance & Evidence