Potassium Cyanide → 3-Pyridineacetonitrile, 6-(trifluoromethyl)-

HRID 1620982Notes

Reaction equation

HRID 1620982 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([F:12])([F:11])[F:10])=[N:7][CH:8]=1.[C-:13]#[N:14].[K+]>C(O)C.O>[F:10][C:9]([F:12])([F:11])[C:6]1[N:7]=[CH:8][C:3]([CH2:2][C:13]#[N:14])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridine

Product 1

HCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-Yield 771%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of Example 85C (2.1 g, 1.08 mmol) in 40 mL of ethanol and 15 mL of water was added KCN (0.84 g, 12.9 mmol). The mixture was refluxed for 6 hours, and then cooled to room temperature. Most of the ethanol was removed under vacuo and the residue was diluted with 25 mL of water. The resulting mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column (petroleum ether:ethyl acetate=20:1) to afford the title compound (1.55 g, 64.7%). 1H NMR (400 MHz, CDCl3): δ 8.78 (s, 1H), 7.77-7.94 (m, 2H), 3.84 (s, 2H).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customMost of the ethanol was removed under vacuo
  3. additionthe residue was diluted with 25 mL of water
  4. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×3)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel column (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-959992f51a444f56b130fe860dcfa9fb
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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