Ethyl Acetate → 6-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrile

HRID 392344Notes

Reaction equation

HRID 392344 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10]C2C=CC(O)=CC=2)=[N:4][CH:3]=1.[N+]([O-])([O-])=O.[Ce+3].[NH4+].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[F:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5](=[O:10])[NH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 14029277Diammonium cerium nitrateHCID 226628546-Fluoro-3-(4-hydroxyphenoxy)-2-pyrazinecarbonitrile

Product 1

HCID 226627856-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

In a mixture of 7.5 mL of acetonitrile and 3 mL of water was dissolved 0.45 g of 6-fluoro-3-(4-hydroxyphenoxy)-2-pyrazinecarbonitrile. Then, 1.17 g of diammonium cerium nitrate was added at room temperature, and stirred at the same temperature as above for 15 minutes. A mixture of 10 mL of ethyl acetate and 5 ml of 5% aqueous solution of sodium thiosulfate was added to the reaction mixture, and the organic layer was separated. The organic layer thus obtained was washed with saturated aqueous solution of sodium chloride, treated with active charcoal and dried on anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. Thus, 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarbonitrile was obtained as a yellow-colored solid product.

Workup

  1. additionwas added to the reaction mixture
  2. customthe organic layer was separated
  3. customThe organic layer thus obtained
  4. washwas washed with saturated aqueous solution of sodium chloride
  5. additiontreated with active charcoal
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6ee4e05a20e04d2388aa1e993b81a563
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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