Methanol → HCID 90389409, compound

Temperature

95 °C

A sealable reaction vessel was charged with 5-hydroxy-3-methylpicolinic acid (0.651 g, 4.25 mmol) and MeOH (35 mL). The reaction vessel was placed in a water bath, and concentrated sulfuric acid (0.854 mL, 15.94 mmol) was added. The vessel was sealed and heated in a 95° C. oil bath. After 24 h, the reaction mixture was concentrated and the residue was taken up in 30 mL of 0.5M aqueous Na2CO3. The aqueous phase was extracted with 10% MeOH-EtOAc (100 mL). The aqueous layer was separated and saturated with NaCl. The aqueous phase was extracted with 10% MeOH-EtOAc (7×100 mL). The combined organic fractions were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography, eluting with 3% to 4% MeOH-DCM to afford the title compound (593 mg). MS m/z=168 (M+H)+.

1. customThe reaction vessel was placed in a water bath
2. customThe vessel was sealed
3. concentrationthe reaction mixture was concentrated
4. extractionThe aqueous phase was extracted with 10% MeOH-EtOAc (100 mL)
5. customThe aqueous layer was separated and saturated with NaCl
6. extractionThe aqueous phase was extracted with 10% MeOH-EtOAc (7×100 mL)
7. dry with materialThe combined organic fractions were dried over MgSO4
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography
10. washeluting with 3% to 4% MeOH-DCM

ORD record

ord-63c654d5b8e44620a801f696a18bec73

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2