Ammonia → 2-Amino-4-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

50 g of 5-ethoxy-3-hydroxy-3-(trifluoromethyl)pent-4-enenitrile were mixed with 600 g of aqueous ammonia (25%), and the resulting mixture was heated to 125° C. in an autoclave for 24 h, in the course of which a pressure of approx. 14 bar built up. Subsequently, the reaction mixture was cooled and the resulting biphasic mixture was extracted repeatedly with dichloromethane. The combined organic phases were cautiously concentrated by rotary evaporation, and the product was subsequently recrystallized from cyclohexane. 26.3 g of 2-amino-4-(trifluoromethyl)pyridine (68%) were thus obtained as a yellowish-brown solid. The spectroscopic data agreed with those reported in the literature (A. D. Dunn et al. in J. Fluorine Chem. 1999, 93, 153-157).

Provenance & Evidence