Reacción #710500

Ecuación de reacción

2-chloro-6-(trifluoromethyl)nicotinaldehyde

sodium hydroxide

nitro methane

→

1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol

Rendimiento 72.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   OtroAfter completion of reaction
3. 3
   Concentraciónthe reaction mixture was concentrated under reduced pressure
4. 4
   Otroto remove nitro methane
5. 5
   Otroquenched with ice water (500 mL)
6. 6
   Extracciónextracted with ethyl acetate (2×1.0 L)
7. 7
   LavadoThe combined organic layer was washed with water (500 mL), brine (500 mL)
8. 8
   Secadodried over anhydrous sodium sulfate
9. 9
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a stirred solution of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (Int-17) (70 g, 1.0 eq.) in nitro methane (700 mL) was added sodium hydroxide (6.7 g, 0.5 eq.) at room temperature. The resulting reaction mixture was heated to 100° C. and stirred for 2 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was concentrated under reduced pressure to remove nitro methane quenched with ice water (500 mL) and extracted with ethyl acetate (2×1.0 L). The combined organic layer was washed with water (500 mL), brine (500 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to get pure 1-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2-nitroethanol (Int-18) (65.0 g, 72.0%).

Fuente