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

HRID 11448Notes

Reaction equation

HRID 11448 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-butenoate (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. An insoluble matter was filtered out, and the filtrate was concentrated under reduced pressure. The resulting crystals were filtered off with acetone to give 0.61 g (60%) of 3-(4-pyridyl)butyric acid 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. filtrationAn 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-327817e6450444259c376fea7bea94c6
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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