Lithium Hydroxide → 6-(Difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 512463Notes

Reaction equation

HRID 512463 reaction equation
[F:1][CH:2]([F:14])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([O:12]C)=[O:11])=[CH:5][CH:4]=1.[OH-].[Li+]>CO.O>[F:14][CH:2]([F:1])[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69233637HCID 69233637, compound

Product 1

HCID 685011126-(Difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7.4 g (36.4 mmol) of methyl 6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate were dissolved in 100 ml of methanol, and a solution of 1.3 g (54.6 mmol) of lithium hydroxide in 50 ml of water was added. After two hours of heating under reflux, the mixture was concentrated to a volume of about 50 ml and the solution was washed with dichloromethane. The aqueous phase was then acidified with 2N hydrochloric acid and extracted with ethyl acetate. Drying and concentration of the extract gave 5.6 g (82% of theory) of a brownish powder.

Workup

  1. temperatureAfter two hours of heating
  2. temperatureunder reflux
  3. concentrationthe mixture was concentrated to a volume of about 50 ml
  4. washthe solution was washed with dichloromethane
  5. extractionextracted with ethyl acetate
  6. customDrying
  7. customconcentration of the extract gave 5.6 g (82% of theory) of a brownish powder

Sources & evidence

ORD record
ord-4f076c617179471f92cab9f88e7137f8
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

Loading…