Phosphorus oxychloride → 2-Methoxy-5-(trifluoromethyl)nicotinonitrile

HRID 2106801Notes

Reaction equation

HRID 2106801 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=[N:10]O)=[CH:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][N:4]=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[C:9]([C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([C:12]([F:15])([F:13])[F:14])[CH:7]=1)#[N:10]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 727398092-Methoxy-5-(trifluoromethyl)-3-pyridinecarboxaldehyde oxime

Product 1

HCID 230489992-Methoxy-5-(trifluoromethyl)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methoxy-5-(trifluoromethyl)-3-pyridinecarboxaldehyde oxime (3.9 g, 0.018 mol) was added to a mixture of 1.9 ml (0.020 mol) of phosphorus oxychloride in 20 ml of acetonitrile and the resulting mixture heated at reflux with stirring for 1 hour. It was then allowed to cool and was poured onto ice. The mixture obtained was extracted several times with methylene chloride and the combined extracts were in turn extracted with saturated aqueous sodium chloride. The methylene chloride solution was dried over sodium sulfate and concentrated by evaporation under reduced pressure to obtain 3.2 g (89 percent of theory of the title compound as a yellow oil which solidified on standing. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux
  3. temperatureto cool
  4. additionwas poured onto ice
  5. customThe mixture obtained
  6. extractionwas extracted several times with methylene chloride
  7. extractionextracted with saturated aqueous sodium chloride
  8. dry with materialThe methylene chloride solution was dried over sodium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-6a92584138f342d4bfe545dd99013050
Source dataset
uspto-grants-1990_06
Patent number
US04931452

Reaction notes

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