Reacción #74767

Ecuación de reacción

hydrochloric acid

sodium nitrite

3-amino-2-hydroxymethylpyridine

hydrochloric acid

→

3-chloro-2-hydroxymethylpyridine

Disolventes

water

hydrogen sulphide

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated on a steam-bath for 0.5 hours
2. 2
   FiltraciónThe mixture was filtered
3. 3
   Concentraciónconcentrated
4. 4
   Extracciónextracted with chloroform
5. 5
   Extracciónthe chloroform extract
6. 6
   Otrowas evaporated

Procedimiento

A solution of sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a mixture of 3-amino-2-hydroxymethylpyridine (4.8 g), aqueous hydrochloric acid (48%, 10 ml) and water (5 ml) stirred at 0°-5°. This solution was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric acid and the mixture was heated on a steam-bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. The mixture was filtered, concentrated and extracted with chloroform and the chloroform extract was evaporated to give 3-chloro-2-hydroxymethylpyridine (3.7 g) m.p. 42°-44° (from n-pentane).

Fuente