Acetonitrile → 4-(2,2,2-Trifluoro-1-methyl-ethyl)pyridine-2-carbonitrile

HRID 1880772

Reaction equation

HRID 1880772 reaction equation
[C:1](#[N:3])C.[F:4][C:5]([F:15])([F:14])[CH:6]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[CH3:7].C[Si](C#N)(C)C>C(N(CC)CC)C>[F:15][C:5]([F:4])([F:14])[CH:6]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:1]#[N:3])[CH:9]=1)[CH3:7]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 82115Trimethylsilyl cyanideHCID 595703374-(2,2,2-Trifluoro-1-methyl-ethyl)pyridine

Product 1

HCID 595703594-(2,2,2-Trifluoro-1-methyl-ethyl)pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

To 8 ml of acetonitrile were added 0.9 g of 4-(2,2,2-trifluoro-1-methyl-ethyl)pyridine=N-oxide, 1.31 ml of triethylamine and 1.4 g of trimethylsilyl cyanide, and the mixture was stirred at 90° C. for 16 hours. Thereafter, the reaction solution was allowed to cool to temperature, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.7 g of 4-(2,2,2-trifluoro-1-methyl-ethyl)pyridine-2-carbonitrile.

Workup

  1. temperatureto cool to temperature
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2962d583b9b645e5b8d8ceb44003d091
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Linked notes

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