Ethanol → 2-(cyclopropylamino)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

A reaction flask equipped with a mechanical stirrer, temperature controller, condenser and addition funnel was charged with 2-chloro-3-pyridinecarbonitrile (69.25 g, 0.50 mol), 300 ml of ethanol and 200 ml of water. With agitation, cyclopropylamine ( 114g, 2.0 mol) was added dropwise over 30 minutes at a temperature<30° C. When the addition was completed, the stirred reaction mixture was heated to reflux temperature for 20 hours. The reaction mixture was cooled to 60° C. and then 350 ml of excess cyclopropylamine and ethanol were removed by vacuum distillation using water aspirator vacuum. The remaining aqueous solution was cooled to ambient temperature and allowed to stand overnight. The solid product was collected by filtration and the filter cake rinsed with water. The yield was 81.51 g (theoretical yield is 79.5 g).

Provenance & Evidence