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

Temperature

125 °C

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).

1. temperatureSubsequently, the reaction mixture was cooled
2. extractionthe resulting biphasic mixture was extracted repeatedly with dichloromethane
3. concentrationThe combined organic phases were cautiously concentrated by rotary evaporation
4. customthe product was subsequently recrystallized from cyclohexane

ORD record

ord-47d5aa89ac5f432686728837428f8b7c

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063226B2