Ethyl 3-(6-methylpyridin-3-yl)-3-oxopropanoate → Ethyl 3-Hydroxy-3-(6-methyl-3-pyridyl)propanoate

HRID 1789221Notes

Reaction equation

HRID 1789221 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[N:9][CH:8]=1)[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([OH:14])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[N:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 89013Ethyl 3-(6-methylpyridin-3-yl)-3-oxopropanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 14178170Ethyl 3-Hydroxy-3-(6-methyl-3-pyridyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10.0 g (0.048 mol) of 6-methyl nicotinoyl acetic acid ethyl ester (distilled) was dissolved in 200 ml of 95 percent ethanol, mixed with 1 g of 5 percent palladium on activated carbon and poured into a 1-liter autoclave. The autoclave was put under 10 bars of hydrogen and stirred at 20°. The hydrogenation ended after 6 hours. The autoclave was opened, and the reaction solution filtered and evaporated. 10.0 g of 3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid ethyl ester remained, which according to NMR and DC was pure. The yield, in relation to the 6-methyl nicotinoyl acetic acid ethyl ester, was 100 percent.

Workup

  1. additionpoured into a 1-liter autoclave
  2. filtrationthe reaction solution filtered
  3. customevaporated

Sources & evidence

ORD record
ord-4a9ec14af0274134a654dea42067722b
Source dataset
uspto-grants-1987_08
Patent number
US04687856

Reaction notes

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