3-Hydroxypicolinic Acid → Methyl 3-Hydroxy-2-pyridinecarboxylate

3-Hydroxypicolinic acid (5.0 g) was dissolved in 350 ml of toluene and 100 ml of methanol. A 2 M solution (25 ml) of trimethylsilyldiazomethane in hexane was added dropwise to the solution, and a reaction was allowed to proceed at room temperature overnight. The reaction solution was concentrated under the reduced pressure. Methylene chloride (100 ml) and water (100 ml) were then added to the concentrate to conduct extraction. The aqueous layer was then extracted with methylene chloride. The organic layer was dried over magnesium sulfate, and was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate-hexane) to give 2.3 g (yield 41%) of methyl 3-hydroxypicolinate.

1. concentrationThe reaction solution was concentrated under the reduced pressure
2. additionMethylene chloride (100 ml) and water (100 ml) were then added to the
3. concentrationconcentrate
4. extractionextraction
5. extractionThe aqueous layer was then extracted with methylene chloride
6. dry with materialThe organic layer was dried over magnesium sulfate
7. concentrationwas concentrated under the reduced pressure
8. customThe residue was purified by column chromatography on silica gel (ethyl acetate-hexane)

ORD record

ord-4a1fad1a10be40f38c7367318426cc13

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183278B1