Lithium hydroxide, monohydrate → 5-Fluoro-6-hydroxypyridine-3-carboxylic acid

To a solution of methyl 5-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylate (0.876 g, 5.12 mmol) in MeOH (33 mL) and water (11 mL), was added lithium hydroxide hydrate (1.074 g, 25.6 mmol). The resulting mixture was then stirred at rt for 5 h. The mixture was concentrated and the pH was adjusted to pH=5 using concentrated HCl. The mixture was then concentrated and dried in vacuo. The resulting residue was dissolved in MeOH (20 mL) and silica gel was added. The mixture was concentrated and dried. The solid mixture was then purified by silica gel flash column chromatography (30%-100% EtOAc/hexane, then 0%-100% MeOH/DCM) to give the title compound as an off-white solid. MS (ESI, positive ion) m/z: 158 (M+H).

1. concentrationThe mixture was concentrated
2. concentrationThe mixture was then concentrated
3. customdried in vacuo
4. dissolutionThe resulting residue was dissolved in MeOH (20 mL)
5. additionsilica gel was added
6. concentrationThe mixture was concentrated
7. customdried
8. customThe solid mixture was then purified by silica gel flash column chromatography (30%-100% EtOAc/hexane

ORD-Eintrag

ord-77fee76dfe88482686c22372d8bb1e90

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09096527B2