Potassium Hydroxide → 3-(Trifluoromethyl)pyrazine-2-carboxylic acid

HRID 2388634Notes

Reaction equation

HRID 2388634 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:4]([C:9]([O:11]C)=[O:10])=[N:5][CH:6]=[CH:7][N:8]=1.[OH-].[K+]>C(O)C.O>[F:14][C:2]([F:1])([F:13])[C:3]1[C:4]([C:9]([OH:11])=[O:10])=[N:5][CH:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58542464Methyl 3-(trifluoromethyl)pyrazine-2-carboxylate

Product 1

HCID 536308603-(Trifluoromethyl)pyrazine-2-carboxylic acidYield 63%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Methyl 3-trifluoromethylpyrazine-2-carboxylate (700 mg, 3.4 mmol) was dissolved in ethanol-water (1:1, 10 ml), followed by adding potassium hydroxide (300 mg) and refluxing under heating for 1 hour. The reaction solution was concentrated under reduced pressure, followed by dilution of residue with water and washing with ethyl acetate. The water layer was acidified with HCl, followed by extracting with ethyl acetate, washing with a saturated brine. The solution was dried over magnesium sulfate, and concentrated under reduced pressure to obtain 409 mg of the desired compound as crystal.

Workup

  1. temperaturerefluxing
  2. temperatureunder heating for 1 hour
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. washwashing with ethyl acetate
  5. extractionby extracting with ethyl acetate
  6. washwashing with a saturated brine
  7. dry with materialThe solution was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb82e8b3aa8b451086c53fd9cc10a841
Source dataset
uspto-grants-2012_09
Patent number
US08269045B2

Reaction notes

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