Methyl iodide → 2-Chloro-3-methoxypyridine

To a solution of 2-chloro-3-hydroxypyridine (25 g; 193 mmol) in N,N-dimethylformamide (250 mL) was added sodium methoxide (11.5 g; 212 mmol). The mixture was stirred for 4 hours at room temperature and methyl iodide (24 mL; 386 mmol) was added. The resulting mixture was stirred for another 16 hours. The reaction mixture was quenched with water and extracted with dichloromethane. The combined extracts were washed with water, dried over sodium sulfate and concentrated under reduced pressure to provide product (13 g) as a yellow oil. The aforementioned product, 2-chloro-3-methoxypyridine (2), was used for the next step without further purification.

1. stirringThe resulting mixture was stirred for another 16 hours
2. customThe reaction mixture was quenched with water
3. extractionextracted with dichloromethane
4. washThe combined extracts were washed with water
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-4cb59668f4fc48fdb7c80a6cd202df4c

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687487B2