Triethylamine → 2-Cyano-1,4-dihydro-1-dimethylamino-5-ethylpyridine

Participants

Reaction Steps

12.6 g of 1-dimethylamino-1-aza-3-ethyl-1,3-butadiene, 8 ml of 2-chloroacrylonitrile and 27.8 ml of triethylamine are heated in 40 ml of dioxane for 31/2 hours to 70° C. The reaction mixture is concentrated by evaporation and the residue is chromatographed over silica gel with a 16:1 mixture of hexane/ethyl acetate, affording 8.2 g of the title compound as a yellow oil which, on standing at room temperature, spontaneously reacts further to 2-cyano-5-ethylpyridine, with elimination of dimethylamine.

Provenance & Evidence