Oxalyl chloride → Methyl 2-chloro-6-methylpyridine-3-carboxylate

To the solution of 2-chloro-6-methylnicotinic acid (5 g, 29.1 mmol) in CH2Cl2 (40 mL) was added oxalyl dichloride (8.1 g, 63.8 mmol) at 0° C. and the reaction mixture was stirred for 2 h. The mixture was concentrated and 40 mL of methanol was then added at 0° C. and the reaction mixture was stirred at RT for 12 h. The mixture was then concentrated in vacuo and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide methyl 2-chloro-6-methylnicotinate that is used without further purification as a light yellow solid.

1. concentrationThe mixture was concentrated
2. addition40 mL of methanol was then added at 0° C.
3. stirringthe reaction mixture was stirred at RT for 12 h
4. concentrationThe mixture was then concentrated in vacuo
5. extractionextracted with EtOAc
6. washThe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-568c4cce789a46f984593b2ddc98f41a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199994B2