HCID 10352231, compound → Ethyl isonicotinylacetate

HRID 2217758Notes

Reaction equation

HRID 2217758 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.[H][H]>CO.[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

5

Reactant 2

HCID 10352231HCID 10352231, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12229233Ethyl isonicotinylacetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl (E)-3-pyridin-4-ylprop-2-enoate (Method 8; 102.3 g, 576 mmol) in MeOH (300 ml) was hydrogenated using palladium on carbon 5% (9.0 g) under atmospheric pressure hydrogen for 72 hours. The catalyst was filtered off through diatomaceous earth and the filtrate concentrated to give a yellow oil. Yield 103.1 g (99%). NMR (300 MHz, CDCl3) 8.50 (d, 2H), 7.15 (d, 2H), 4.12 (q, 2H), 2.95 (t, 2.64 (t, 2H), 1.21 (t, 3H); m/z 180.4.

Workup

  1. customfor 72 hours
  2. filtrationThe catalyst was filtered off through diatomaceous earth
  3. concentrationthe filtrate concentrated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-70945e8197c0425aa1adf11412de0bf9
Source dataset
uspto-grants-2008_08
Patent number
US07408064B2

Reaction notes

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