Реакция #40583

Уравнение реакции

calcium carbonate

benzyltrimethylammonium dichloroiodate

5-amino-2-chloropyridine

→

expected product

Выход 39.1%

3-Amino-6-chloro-2-iodopyridine

Выход 39.1%

Растворители

methanol

dichloro-methane

Условия реакции

Обработка

1. 1
   Фильтрацияfiltered
2. 2
   Другоеto remove the mineral salts
3. 3
   workup.ADDITIONThe filtrate is diluted with water
4. 4
   Экстракцияextracted with DCM
5. 5
   ДругоеThe organic phase obtained
6. 6
   Промывкаis washed with sodium chloride solution
7. 7
   Сушкаwith saturated sodium thiosulfate solution, dried over magnesium sulfate
8. 8
   Концентрированиеconcentrated under reduced pressure
9. 9
   ДругоеAn oil is obtained
10. 10
    Другоеwhich is purified by chromatography on silica gel
11. 11
    Промывкаeluting with a cyclohexane/ethyl acetate mixture (80/20

Методика

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%).

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