Carbon Tetrachloride → Methyl 2-methoxypyridine-3-carboxylate

A mixture of 2-methoxy-nicotinic acid (5.00 g, 32.6 mmol), thionyl chloride (50 mL) and carbon tetrachloride (50 mL) was head at reflux for 2 h. The reaction mixture was allowed to cool and volatiles were removed on a rotary evaporator. The residue was co-evaporated three times with carbon tetrachloride to remove residual oxalyl chloride. Methanol (50 mL) was added and the mixture was stirred at room temperature overnight. The solvent was evaporated and chloroform (150 mL) was added. The solution was washed with saturated aqueous sodium hydrogen carbonate (2×150 mL) and brine (150 mL), dried (magnesium sulfate), filtered, and evaporated to give 2-methoxy-nicotinic acid methyl ester (4.42 g, 81%) as a clear yellow oil.

1. temperatureat reflux for 2 h
2. temperatureto cool
3. customvolatiles were removed on a rotary evaporator
4. customto remove residual oxalyl chloride
5. additionMethanol (50 mL) was added
6. customThe solvent was evaporated
7. additionchloroform (150 mL) was added
8. washThe solution was washed with saturated aqueous sodium hydrogen carbonate (2×150 mL) and brine (150 mL)
9. dry with materialdried (magnesium sulfate)
10. filtrationfiltered
11. customevaporated

ORD record

ord-c4d0d4f2c4464488ae29c8a58e7b3545

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622492B2