Phosphorus oxychloride → 5-Acetyl-3-pyridinecarbonitrile

HRID 1491839Notes

Reaction equation

HRID 1491839 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-825ce53b496c41359a5e94f82879672c
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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