Lithium hydroxide, monohydrate → 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid

HRID 512451Notes

Reaction equation

HRID 512451 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[NH:3]1.O.[OH-].[Li+]>CO.O>[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[C:4]([C:12]([F:14])([F:13])[F:15])[NH:3]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15217844Methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 27751162-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

At room temperature, 4.73 g (21.4 mmol) of methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate were dissolved in 45 ml of methanol and 15 ml of water, 1.80 g (42.8 mmol) of lithium hydroxide monohydrate were added and the mixture was then heated under reflux for 2 h. The mixture was concentrated to about 15 ml and then washed with dichloromethane and the aqueous phase was adjusted to pH 2 by addition of 2N hydrochloric acid. The mixture was again extracted with dichloromethane, and the organic phase was dried and concentrated. This gave 4.2 g (94% of theory) of a colorless powder.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe mixture was concentrated to about 15 ml
  4. washwashed with dichloromethane
  5. additionthe aqueous phase was adjusted to pH 2 by addition of 2N hydrochloric acid
  6. extractionThe mixture was again extracted with dichloromethane
  7. customthe organic phase was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6925a83614a641c1b071b806ee2b408a
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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