Butyl nitrite → alpha-Oximino-3-pyridylacetonitrile

Participants

Reaction Steps

To a stirred solution of sodium ethoxide in anhydrous ethanol, prepared from 5 g of sodium and 50 ml of anhydrous ethanol, 24 g of 3-pyridineacetonitrile was added, followed by dropwise addition of 21 g freshly distilled n-butyl nitrite. The reaction mixture was stirred for another hour and the precipitated sodium salt of the oxime was filtered and washed with ether. The free oxime was obtained by acidification of an aqueous solution of the salt and recrystallization from water, yielding 17 g (58%) of the title compound. M.p. 234°-238° C. under decomposition. Usually, the salt was directly used in succeeding reactions.

Provenance & Evidence