Potassium Carbonate → HCID 117770282, compound

HRID 1526383Notes

Reaction equation

HRID 1526383 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].[F:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([F:22])[C:14]=1F.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O>[F:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[C:15]([F:22])[C:14]=1[N:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:10]#[N:11])[C:5]1=[O:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27827931,2,3-Trifluoro-5-nitrobenzeneHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-

Product 1

HCID 117770282HCID 117770282, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (2.00 g), 1,2,3-trifluoro-5-nitrobenzene (3.54 g), potassium carbonate (3.73 g) and N,N-dimethylformamide (20 mL) was stirred at room temperature for 2 hr. The reaction mixture was slowly poured into saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the residue was added a mixed solvent (10 mL) of isopropyl ether/ethyl acetate=4/1, and the mixture was stirred for 15 min. The precipitate was collected by filtration to give the title compound (3.75 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionTo the residue was added a mixed solvent (10 mL) of isopropyl ether/ethyl acetate=4/1
  6. stirringthe mixture was stirred for 15 min
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-66bece1a3d6f4fbd87ecc70b68d925b8
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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