6-(3-Pyridinyl)-5-hexynenitrile → 6-(Pyridin-3-YL)hexanenitrile

HRID 745517Notes

Reaction equation

HRID 745517 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])[CH:2]=1.[H][H]>CC(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])[CH:2]=1

Participants

5

Reactant 2

HCID 137397376-(3-Pyridinyl)-5-hexynenitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 129045566-(Pyridin-3-YL)hexanenitrileYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 62.82 g of 6-(3-pyridinyl)-5-hexynenitrile in 500 ml of 2-propanol was hydrogenated over 3.0 g of 10% palladium on carbon at atmospheric pressure. Two additional 3.0 g charges of catalyst were added as the rate of hydrogen uptake slowed. After two days, the reaction mixture was filtered, concentrated, the residue was evaporatively distilled and the distillate was dissolved in 300 ml of 2-propanol and was reduced over 3.0 g of 10% palladium on carbon. Filtration, evaporation, and distillation gave 52.15 g (82%) of 6-(3-pyridinyl)hexanenitrile, bp 150°/0.3 mm which gave a main peak consisting of 93% of the total by gas chromatography analysis. A portion was further purified by silica gel chromatography eluting with 1:1 ethyl acetate-hexane containing 1% triethyl amine and was evaporatively distilled to give an analytical sample.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. distillationthe residue was evaporatively distilled
  4. dissolutionthe distillate was dissolved in 300 ml of 2-propanol
  5. filtrationFiltration, evaporation, and distillation

Sources & evidence

ORD record
ord-64a8947d1dde4a76b04eaf450eeb0c7d
Source dataset
uspto-grants-1986_07
Patent number
US04599336

Reaction notes

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