Water → HCID 19365501, compound

HRID 849930Notes

Reaction equation

HRID 849930 reaction equation
F[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]2[C:12](=[O:22])[N:13]([CH3:21])[C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][N:16]=2)=[CH:4][CH:3]=1.[F-].[K+].[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:28])[CH2:26][OH:27].O>O1CCOCC1>[CH2:30]([O:29][C:25]([CH2:26][O:27][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]2[C:12](=[O:22])[N:13]([CH3:21])[C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][N:16]=2)=[CH:4][CH:3]=1)=[O:28])[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 81882Butyl GlycolateHCID 522689Potassium FluorideHCID 19365524HCID 19365524, compound2×

Product 1

HCID 19365501HCID 19365501, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Then, 1.10 g of 3-(4-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-13) was dissolved in 4.0 ml of 1,4-dioxane, to which 0.812 g of potassium fluoride and 0.925 g of butyl glycolate, and the mixture was heated under reflux for 1.5 hours. After completion of the reaction, the reaction mixture was left cooling to room temperature. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 1.25 g (yield, 83%) of 3-[4-(butoxycarbonylmethoxy)-5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (the present compound depicted below).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. customAfter completion of the reaction
  4. waitthe reaction mixture was left
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-78c7cfb9aaec4f7bb930551c4e9250c4
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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