Ammonium Chloride → 2-Amino-4-cyano-4-ethoxy-butyronitrile

Participants

Reaction Conditions

Reaction Steps

51.5 millimoles of ethoxy-acrylonitrile are dissolved in 10 ml of anhydrous toluene at 60° C. under an argon atmosphere. 77.25 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (51.5 ml) are added, dropwise, at -60° C. After stirring at this temperature for 45 minutes, 7.7 ml (1.1 eq) of trimethylsilyl cyanide are added to the reaction mixture at -50° C. The latter is maintained at -50° C. for 3 hours while stirring, then hydrolyzed by ammonium chloride then water. After purification of the so-obtained aminonitrile, by liquid chromatography on silica (elution with ethyl acetate/petroleum ether 1/1), 1.7 g of 2-amino-4-cyano-4-ethoxy-butyronitrile are obtained in a form of an orange-colored oil.

Provenance & Evidence