Phosphorus oxychloride → 5-Acetyl-3-pyridinecarbonitrile

HRID 2379822Notes

Reaction equation

HRID 2379822 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15](=O)[NH2:16])[CH:14]=1)(=[O:8])[CH3:7]>CN(C)C=O>[C:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 226073883-Pyridinecarboxamide, 5-acetyl-

Product 1

HCID 189537855-Acetyl-3-pyridinecarbonitrileYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride (2.75 g) was added to a solution of 3-acetyl-5-carbamoylpyridine (2.8 g) in N,N-dimethylformamide (30 ml) with cooling on an ice-water bath. The mixture was stirred with cooling for 1.5 hours. The solvent was removed under reduced pressure. The residue was dissolved in water (150 ml) and the mixture was extracted with ethyl acetate (100 ml). The extract was dried with magnesium sulfate and then evaporated. The residue was chromatographed on a silica gel column eluting with chloroform to afford 3-acetyl-5-cyanopyridine (1.21 g).

Workup

  1. temperaturewith cooling on an ice-water bath
  2. temperaturewith cooling for 1.5 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water (150 ml)
  5. extractionthe mixture was extracted with ethyl acetate (100 ml)
  6. dry with materialThe extract was dried with magnesium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on a silica gel column
  9. washeluting with chloroform

Sources & evidence

ORD record
ord-c7a44f96e5cc4d408dd1ebcf43f7f1f2
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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