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

HRID 1740998Notes

Reaction equation

HRID 1740998 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N1CCCCC1>N1C=CC=CC=1>[N:1]1[CH:2]=[CH:3][C:4]([CH:7]=[CH:10][C:11]([OH:13])=[O:12])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 953033-(4-Pyridinyl)-2-propenoic acidYield 76.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Pyridinecarboxaldehyde (18.96 g, 0.177 mol) and malonic acid (55.3 g, 0.53 mol) were placed in 200 ml of pyridine. Piperidine (5.25 ml, 0.053 mol) was added and the reaction was refluxed for 6 hours. The reaction mixture was cooled in an ice bath and then the white solid was filtered off and rinsed with ether and dried to afford 20.1 g of the subtitle compound. Concentration of the filtrate and then filtration and rinsing with ether resulted in recovery of another 2.2 g of product (84% total yield).

Workup

  1. temperaturethe reaction was refluxed for 6 hours
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. filtrationthe white solid was filtered off
  4. washrinsed with ether
  5. customdried

Sources & evidence

ORD record
ord-92c09baf71f24ea8b041649676f053a6
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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