3-(3-Pyridinyl)-2-propenenitrile → 3-(Pyridin-3-yl)propanenitrile

HRID 1594647Notes

Reaction equation

HRID 1594647 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]#[N:10])[CH:2]=1>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]#[N:10])[CH:2]=1

Participants

4

Reactant 1

HCID 537301363-(3-Pyridinyl)-2-propenenitrile

Product 1

HCID 100119303-(Pyridin-3-yl)propanenitrileYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

49.5 g (0.38 mol) of 3-(3-pyridyl)-acrylonitrile is dissolved in 428 ml of ethanol, 9.5 g of 10% Pd/C is added and hydrogenated under normal pressure. After the requisite hydrogen absorption, it is filtered off, and the filtrate is concentrated by evaporation in a vacuum. Chromatography (CH2Cl2→CH2Cl2/acetone 1:4) yields 38.3 g (76%) of 3-(3-pyridyl)propionitrile.

Workup

  1. customAfter the requisite hydrogen absorption, it
  2. filtrationis filtered off
  3. concentrationthe filtrate is concentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-f1dafe51fedb46caa45836f86dcc1d29
Source dataset
uspto-grants-2001_09
Patent number
US06284779B1

Reaction notes

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