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

HRID 392343Notes

Reaction equation

HRID 392343 reaction equation
C(OC1C=CC([O:13][C:14]2[C:15]([C:21]#[N:22])=[N:16][C:17]([F:20])=[CH:18][N:19]=2)=CC=1)C1C=CC=CC=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:20][C:17]1[N:16]=[C:15]([C:21]#[N:22])[C:14](=[O:13])[NH:19][CH:18]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 14029277Diammonium cerium nitrateHCID 226628343-[4-(Benzyloxy)phenoxy]-6-fluoro-2-pyrazinecarbonitrile

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

In a mixture of 30 mL of acetonitrile and 15 mL of water was dissolved 1.0 g of 3-[4-(benzyloxy)phenoxy]-6-fluoro-2-pyrazinecarbonitrile. After adding 8.5 g of diammonium cerium nitrate, the mixture thus obtained was heated under reflux for 3 hours. The reaction mixture was returned to room temperature, a mixture consisting of 50 mL of ethyl acetate, 5 ml of water and 5 mL of 5% aqueous solution of sodium thiosulfate was added, 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. customthe mixture thus obtained
  2. temperaturewas heated
  3. temperatureunder reflux for 3 hours
  4. customwas returned to room temperature
  5. additionwas added
  6. customthe organic layer was separated
  7. customThe organic layer thus obtained
  8. washwas washed with saturated aqueous solution of sodium chloride
  9. additiontreated with active charcoal
  10. dry with materialdried on anhydrous magnesium sulfate
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-87c12236ab3e4649a86e3b6f8710198d
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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