Water → 6-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrile

HRID 392340Notes

Reaction equation

HRID 392340 reaction equation
C([O:8][C:9]1[C:10]([C:16]#[N:17])=[N:11][C:12]([F:15])=[CH:13][N:14]=1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].O>C1(C)C=CC=CC=1>[F:15][C:12]1[N:11]=[C:10]([C:16]#[N:17])[C:9](=[O:8])[NH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 22662806HCID 22662806, compound

Product 1

HCID 226627856-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 10 mL of toluene was dissolved 1.0 g of 3-(benzyloxy)-6-fluoro-2-pyrazinecarbonitrile. Then, 0.64 g of aluminum chloride was added to the solution at an ice-cooled temperature, and the mixture thus formed was stirred at room temperature for 2 hours. Then, 10 mL of water was added to the reaction mixture, the aqueous layer was separated, and the organic layer was extracted with two 2 mL portions of water. The aqueous layers were united and extracted with two 5 mL portions of ethyl acetate. The organic layer thus obtained was washed with saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Thus, 0.51 g of 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarbonitrile was obtained as a yellow-colored solid product.

Workup

  1. temperaturecooled temperature
  2. customthe mixture thus formed
  3. customthe aqueous layer was separated
  4. extractionthe organic layer was extracted with two 2 mL portions of water
  5. extractionextracted with two 5 mL portions of ethyl acetate
  6. customThe organic layer thus obtained
  7. washwas washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried on anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f84977a61dc24b77a517afdb85952447
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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