Lithium hydroxide, monohydrate → 1-(Difluoromethyl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 2370822Notes

Reaction equation

HRID 2370822 reaction equation
[F:1][CH:2]([F:14])[N:3]1[C:8](=[O:9])[CH:7]=[CH:6][C:5]([C:10]([O:12]C)=[O:11])=[CH:4]1.O.[OH-].[Li+]>CO.O>[F:14][CH:2]([F:1])[N:3]1[C:8](=[O:9])[CH:7]=[CH:6][C:5]([C:10]([OH:12])=[O:11])=[CH:4]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 16079629HCID 16079629, compound

Product 1

HCID 218858751-(Difluoromethyl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 1-(difluoromethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate (0.500 g, 2.461 mmol) in MeOH (12 mL) and water (4 mL) was added lithium hydroxide hydrate (0.207 g, 4.92 mmol, Aldrich). The resulting mixture was then stirred at room temperature for 4 h. Solvent (MeOH) was removed in vacuok, and the remaining aqueous solution was adjusted to pH=5-6 by addition of concentrated HCl. The mixture was then extracted with EtOAc (3×10 mL). The combined organic layers were dried (MgSO4), and the solvent removed to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 190 (M+H).

Workup

  1. customSolvent (MeOH) was removed in vacuok
  2. additionthe remaining aqueous solution was adjusted to pH=5-6 by addition of concentrated HCl
  3. extractionThe mixture was then extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-11feac23ce4f4d39a84df5b83992595a
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

Loading…