2-Chlorobenzonitrile → propiophenone O-(2-cyanophenyl)oxime

HRID 1761912Notes

Reaction equation

HRID 1761912 reaction equation
[C:1](=[N:10][OH:11])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].[H-].[Na+].Cl[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18]>CN(C)C=O>[C:17]([C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[O:11][N:10]=[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][CH3:3])#[N:18]

Participants

5

Reactant 3

HCID 133912-ChlorobenzonitrileHCID 24758Sodium hydrideHCID 347963HCID 347963, compound

Product 1

HCID 54068052propiophenone O-(2-cyanophenyl)oximeYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5.0 g of propiophenone oxime in 35 ml of dimethylformamide is added dropwise to a solution of 1.55 g of 62.5% sodium hydride in 80 ml of dimethylformamide under ice-colling, and the mixture is stirred at the same temperature for 20 minutes. A solution of 4.24 g of 2-chlorobenzonitrile in 20 ml of dimethylformamide is added dropwise to the mixture and the mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into ice-water and the aqueous mixture is extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=6:1) to give 2.19 g of propiophenone O-(2-cyanophenyl)oxime as oil.

Workup

  1. stirringthe mixture is stirred at room temperature for 3 hours
  2. extractionthe aqueous mixture is extracted with ethyl acetate
  3. washThe extract is washed with a saturated sodium chloride solution
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-7e1dfbd9a2a54ddfbac6956fc8fcabee
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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