Cesium carbonate → HCID 117770114, compound

HRID 1526389Notes

Reaction equation

HRID 1526389 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].Cl[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:5](=[O:9])[C:4]=1[C:10]#[N:11]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 27357814-Chloro-3-nitropyridineHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-

Product 1

HCID 117770114HCID 117770114, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (3.00 g), 4-chloro-3-nitropyridine (6.34 g), cesium carbonate (13.02 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 16 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 isopropyl ether (20 mL), and the mixture was stirred for 15 min. The precipitate was collected by filtration to give the title compound (5.00 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 isopropyl ether (20 mL)
  6. stirringthe mixture was stirred for 15 min
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-69916a31585c4164b1a1173f144d0f64
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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