Ethyl 3-(pyridin-4-yl)acrylate → Ethyl isonicotinylacetate

HRID 1741000Notes

Reaction equation

HRID 1741000 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:3][CH:2]=1>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 53396309Ethyl 3-(pyridin-4-yl)acrylate

Product 1

HCID 12229233Ethyl isonicotinylacetateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-(4-pyridyl)acrylate (16.62 g, 93.8 mmol) was hydrogenated in 80 ml of ethanol over 5% Pd on carbon (2 g) at 60 psi at room temperature for 16 hours. After evaporation, the residue was dissolved in 200 ml of diethyl ether and filtered through diatomaceous silica and concentrated to afford 15.97 g (95% yield) of the subtitle compound. D. Preparation of thyl 3-(4-(2-hydroxymethyl)pyridyl)propionate

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in 200 ml of diethyl ether
  3. filtrationfiltered through diatomaceous silica
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-581b53ac4ceb4b49b073dfda9786d506
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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