Reacción #73181

Ecuación de reacción

sodium hydroxide

2-hydroxymethyl-3-pyridinecarboxamide

phosphorus oxychloride

water

→

3-cyano-2-(chloromethyl)pyridine

Disolventes

toluene

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais heated to 81° C. for 2 hours
2. 2
   TemperaturaAfter cooling at 22° C.
3. 3
   Temperaturawith cooling
4. 4
   OtroAfter phase separation
5. 5
   Lavadothe organic phase is washed with 100 ml of water
6. 6
   OtroRemoval of the organic phase and evaporation of the solvent under reduced pressure
7. 7
   Otrogives rise initially to an oily residue which
8. 8
   Otrocrystallizes

Procedimiento

20.0 g (131.45 mmol) of 2-hydroxymethyl-3-pyridinecarboxamide are suspended in 110 ml of acetonitrile and heated to 78° C. Within 15 minutes, 60.65 g (395.52 mmol) of phosphorus oxychloride are metered in and the mixture is heated to 81° C. for 2 hours. After cooling at 22° C., the reaction mixture is stirred into 200 ml of water at 40° C. After 100 ml of toluene have been added, the mixture is neutralized with sodium hydroxide solution with cooling. After phase separation, the organic phase is washed with 100 ml of water. Removal of the organic phase and evaporation of the solvent under reduced pressure gives rise initially to an oily residue which crystallizes on standing.

Fuente