Hydrochloric Acid → 2-Chloro-3-iodo-4-methylpyridine

Temperature

0 °C

A mixture of 2-chloro-4-methylpyridin-3-amine (1.0 g, 7.0 mmol) and concentrated hydrochloric acid (4.4 mL) was cooled to 0° C. and a solution of sodium nitrite (0.5 g, 7.5 mmol) in water (8 mL) was added dropwise. The mixture was stirred for 1 hour at 0° C. and then was added dropwise to a stirred solution of potassium iodide (1.6 g, 9.6 mmol) in water (9 mL). The mixture was warmed to ambient temperature and stirred overnight. The mixture was extracted with diethyl ether and the organic phase was washed with aqueous sodium thiosulphate, brine, dried (MgSO4) and evaporated in vacuo. The crude product was recrystallized from hexane to give the title compound (0.88 g, 47%) as a white solid.

1. temperatureThe mixture was warmed to ambient temperature
2. stirringstirred overnight
3. extractionThe mixture was extracted with diethyl ether
4. washthe organic phase was washed with aqueous sodium thiosulphate, brine
5. dry with materialdried (MgSO4)
6. customevaporated in vacuo
7. customThe crude product was recrystallized from hexane

ORD record

ord-c52d24e593ba4ac082ea59c15fb19a41

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450341B2