Acetonitrile → 4-(Trifluoromethyl)pyridine-2-carbonitrile

HRID 1880716Notes

Reaction equation

HRID 1880716 reaction equation
[C:1](#[N:3])C.[F:4][C:5]([F:13])([F:12])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.C[Si](C#N)(C)C>C(N(CC)CC)C>[F:4][C:5]([F:13])([F:12])[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:1]#[N:3])[CH:7]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 82115Trimethylsilyl cyanideHCID 1380554-(Trifluoromethyl)pyridine

Product 1

HCID 203104534-(Trifluoromethyl)pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To 70 ml of acetonitrile were added 6 g of 4-trifluoromethylpyridine=N-oxide, 10.26 ml of triethylamine, and 10.95 g of trimethylsilyl cyanide, and the mixture was stirred at 90° C. for 20 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 4.5 g of 4-trifluoromethylpyridine-2-carbonitrile.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8d71aa5a42464316a40d8c4810a0f2da
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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