Acrylonitrile → HCID 67547139, compound

HRID 2356748Notes

Reaction equation

HRID 2356748 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:22](#[N:25])[CH:23]=[CH2:24].[Cl-].[NH4+]>CN(C)C=O>[C:22]([CH2:23][CH2:24][CH:9]([NH:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:19][CH:18]=1)[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11])#[N:25]

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59385070HCID 59385070, compound

Product 1

HCID 67547139HCID 67547139, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[2-(4-fluorobenzoyl)aminoacetyl]-pyridine (500 mg) in N,N-dimethylformamide (10 ml) were added sodium hydride (81.3 mg, 60% mineral oil) and acrylonitrile (113 mg) under dry ice-acetone cooling, and the mixture was stirred at the same temperature under argon atmosphere for 10 minutes. The mixture was warmed slowly to 0° C. and stirred at the same temperature for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to obtain a crude product of 4-cyano-2-(4-fluorobenzoylamino)-1-(3-pyridyl)-1-butanone (500 mg).

Workup

  1. stirringstirred at the same temperature for 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ae5e74c4cfb1428aa3ce7f5470a16abd
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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