Acetonitrile → 6-Chloro-4-(trifluoromethyl)pyridine-2-carbonitrile

HRID 1880718Notes

Reaction equation

HRID 1880718 reaction equation
[C:1](#[N:3])C.[Cl:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][N+:6]=1[O-].C[Si](C#N)(C)C>C(N(CC)CC)C>[Cl:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:1]#[N:3])[N:6]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 82115Trimethylsilyl cyanideHCID 19066096HCID 19066096, compound

Product 1

HCID 595703326-Chloro-4-(trifluoromethyl)pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 16 ml of acetonitrile were added 1.5 g of 2-chloro-4-trifluoromethylpyridine N-oxide, 2.12 ml of triethylamine, and 2.26 g of trimethylsilyl cyanide, and the mixture was heated to reflux for 23 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.9 g of 2-chloro-6-cyano-4-trifluoromethylpyridine.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 23 hours
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0aac6075075942b5b0b7dcab1f80c5cc
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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