Malonic Acid → 3-(4-Pyridinyl)-2-propenoic acid

HRID 1862535Notes

Reaction equation

HRID 1862535 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N1C=CC(C=O)=CC=1>C(O)C>[N:8]1[CH:13]=[CH:12][C:11]([CH:1]=[CH:2][C:3]([OH:5])=[O:4])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 1049PyridineHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 953033-(4-Pyridinyl)-2-propenoic acidYield 72.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of malonic acid (12 g), pyridine (7.6 g) in ethanol(41 ml) was added dropwise 4-pyridinecarbaldehyde (10.3 g) at 40° C. The mixture was stirred at 80° C. for 5 hours, then cooled to room temperature. The precipitate was filtered washed with ethanol and dried in vacuo to give 3-(4-pyridyl)-2-propenoic acid (10.4 g)

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dd35c54eacba45af953a5e660cd9d58c
Source dataset
uspto-grants-2003_03
Patent number
US06538007B1

Reaction notes

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