Acetic Acid → 3-(Pyridin-4-yl)butanoic acid

HRID 18391Notes

Reaction equation

HRID 18391 reaction equation
C(O)(=O)C.[N:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:23])=[CH:12][C:13]([O:15]CC2C=CC=CC=2)=[O:14])=[CH:7][CH:6]=1>CO>[N:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:23])[CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 67118931Benzyl 3-(4-pyridyl)-2-butenoate

Product 1

HCID 51859043-(Pyridin-4-yl)butanoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, methanol (31 ml) and acetic acid (0.71 ml, 12.4 mmol) were added to benzyl 3-(4-pyridyl)-2-butenate (1.75 g, 6.20 mmol), and a nitrogen gas was bubbled through the mixture at room temperature for 10 minutes. A catalytic amount of 10%-palladium on carbon was added to the mixture, and the whole was stirred under a hydrogen atmosphere at room temperature overnight. The resulting insoluble matter was filtered out, and the filtrate was concentrated under reduced pressure. The resulting crystals were filtered off with acetone to give 3-(4-pyridyl)butyric acid (0.61 g, 60%) as pale yellow crystals.

Workup

  1. customa nitrogen gas was bubbled through the mixture at room temperature for 10 minutes
  2. additionA catalytic amount of 10%-palladium on carbon was added to the mixture
  3. filtrationThe resulting insoluble matter was filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. filtrationThe resulting crystals were filtered off with acetone

Sources & evidence

ORD record
ord-c3497d1029f54f3583f9b54921fbd056
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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