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Dimethylformamide → 1-(2-Cyanophenyl)-3-(2-pyridyl)-5-phenyl-1,2-dihydropyridin-2-one

HRID 229672
Notes
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Reaction equation

HRID 229672 reaction equation
CN(C)C=O.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:13](=[O:24])[NH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=1.[H-].[Na+].F[C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[C:30]#[N:31]>O>[C:30]([C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[N:14]1[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=[C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]=2)[C:13]1=[O:24])#[N:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 678552-FluorobenzonitrileHCID 223192533-(2-pyridyl)-5-phenyl-2(1H)-pyridone

Product 1

HCID 223190801-(2-Cyanophenyl)-3-(2-pyridyl)-5-phenyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
100 °C

Procedure

5 ml of a dimethylformamide solution containing 0.26 g of 3-(2-pyridyl)-5-phenyl-2 (1H)-pyridone was incorporated with 0.04 g of sodium hydride. After 15 minutes, the solution was further incorporated with 0.15 g of 2-fluorobenzonitrile and 0.10 g of cuprous iodide, and vigorously stirred at 100° C. for 2 hours. The solution was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and then saturated saline water, and dried by magnesium sulfate anhydride. The solvent was distilled off under a vacuum. The residue was refined by silica gel chromatography (ethyl acetate/hexane=1:2), to obtain 0.03 g of the light yellow, powdery subject compound.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialsaturated saline water, and dried by magnesium sulfate anhydride
  5. distillationThe solvent was distilled off under a vacuum
  6. customto obtain 0.03 g of the light yellow, powdery subject compound

Sources & evidence

ORD record
ord-e74409e8db6c4811adf1f68727eea479
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07563811B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes