Reacción #40583

Ecuación de reacción

calcium carbonate

benzyltrimethylammonium dichloroiodate

5-amino-2-chloropyridine

→

expected product

Rendimiento 39.1%

3-Amino-6-chloro-2-iodopyridine

Rendimiento 39.1%

Disolventes

methanol

dichloro-methane

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfiltered
2. 2
   Otroto remove the mineral salts
3. 3
   workup.ADDITIONThe filtrate is diluted with water
4. 4
   Extracciónextracted with DCM
5. 5
   OtroThe organic phase obtained
6. 6
   Lavadois washed with sodium chloride solution
7. 7
   Secadowith saturated sodium thiosulfate solution, dried over magnesium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroAn oil is obtained
10. 10
    Otrowhich is purified by chromatography on silica gel
11. 11
    Lavadoeluting with a cyclohexane/ethyl acetate mixture (80/20

Procedimiento

23.2 g (180.5 mM) of 5-amino-2-chloropyridine are mixed in 70 ml of dichloro-methane (DCM) and 180 ml of methanol, and 21.6 g (216 mM) of calcium carbonate and 75.3 g (226 mM) of benzyltrimethylammonium dichloroiodate are added. The reaction mixture is stirred at room temperature for 16 hours, and then filtered to remove the mineral salts. The filtrate is diluted with water and extracted with DCM. The organic phase obtained is washed with sodium chloride solution, and then with saturated sodium thiosulfate solution, dried over magnesium sulfate and concentrated under reduced pressure. An oil is obtained, which is purified by chromatography on silica gel, eluting with a cyclohexane/ethyl acetate mixture (80/20 and then 70/30; v/v). 13.9 g of the expected product are thus obtained in the form of an orange-colored solid (yield=30%).

Fuente