Dimethylformamide → 5-Chloro-4-(trifluoromethyl)-2-pyridinecarbonitrile

HRID 1880723Notes

Reaction equation

HRID 1880723 reaction equation
[CH3:1][N:2](C)C=O.Cl[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[C:10]([Cl:17])=[CH:9][N:8]=1>[C-]#N.[Zn+2].[C-]#N.O>[Cl:17][C:10]1[C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]([C:1]#[N:2])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 269860162,5-Dichloro-4-(trifluoromethyl)pyridine

Product 1

HCID 595703895-Chloro-4-(trifluoromethyl)-2-pyridinecarbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To 14 ml of N,N-dimethylformamide were added 1 g of 2,5-dichloro-4-trifluoromethylpyridine, 1.71 g of zinc cyanide and 0.34 g of tetrakistriphenylphosphine palladium, and the mixture was stirred at 90° C. for 10 hours. After allowing to cool, the reaction solution was poured into water, and the resultant solution was extracted with diethyl ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.7 g of 5-chloro-4-trifluoromethylpyridine-2-carbonitrile.

Workup

  1. temperatureto cool
  2. extractionthe resultant solution was extracted with diethyl ether three times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec1490629a9241e5b950aa754544d600
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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