(E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoate → 3-(3-Hydroxy-2-pyridyl)-propionic acid methyl ester

HRID 55259Notes

Reaction equation

HRID 55259 reaction equation
[CH3:1][O:2][C:3](=[O:20])/[CH:4]=[CH:5]/[C:6]1[C:11]([O:12]CC2C=CC=CC=2)=[CH:10][CH:9]=[CH:8][N:7]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 1

HCID 22161738(E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoate

Product 1

HCID 545149013-(3-Hydroxy-2-pyridyl)-propionic acid methyl esterYield 87.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In an autoclave, a solution of 11.5 g of 3-(3-benzyloxy-2-pyridyl)-(2E)-2-propenoic acid methyl ester in 125 ml of methanol is hydrogenated in the presence of 1.15 g of 10% palladium catalyst on activated carbon at an initial pressure of 32 bars for 2 hours at room temperature. The reaction mixture is filtered, the filter residue is washed with methanol and the filtrate is concentrated by evaporation. 6.8 g of 3-(3-hydroxy-2-pyridyl)-propionic acid methyl ester of melting point 94°-96° C. is obtained.

Workup

  1. customfor 2 hours
  2. customat room temperature
  3. filtrationThe reaction mixture is filtered
  4. washthe filter residue is washed with methanol
  5. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-36ad5bf363684ec5a11a9a75a7cb889b
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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