Sodium Hydroxide → 4-Iodo-2-methoxypyridine-3-carboxylic acid

To a solution of methyl 4-iodo-2-methoxynicotinate (10 g) in methanol (136 mL) was added 1N aqueous sodium hydroxide solution (136 mL) under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure to evaporate the methanol, and the remaining aqueous solution was washed twice with diethyl ether. The obtained aqueous layer was acidified with 1N hydrochloric acid (about 30 mL), and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (7.7 g).

1. temperaturecooling
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customto evaporate the methanol
4. washthe remaining aqueous solution was washed twice with diethyl ether
5. extractionthe mixture was extracted twice with ethyl acetate
6. washThe combined organic layers were washed with saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-a9848db81025468992b37bc51bc2837a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371320B2