Triethylamine → 5-Ethylpicolinonitrile

Participants

Reaction Steps

39.3 g of 1-dimethylamino-1-aza-3-ethyl-1,3-butadiene, 35 g of 2-chloroacrylonitrile and 112 ml of triethylamine are stirred in 400 ml of acetonitrile for 7 hours at 70° C. The brown reaction mixture is cooled and then filtered and concentrated by evaporation. The residue is dissolved in dioxane and gaseous HCl is introduced. The batch is stirred for 1 hour at room temperature, then concentrated by evaporation, and the residue is partitioned between chloroform and 2N sodium carbonate solution. The organic phase is separated, dried and concentrated by evaporation. The oily residue is distilled under a high vacuum, affording 30.6 g of a yellowish oil with a boiling point of 75°-79° C./3·10-1 mbar.

Provenance & Evidence