Malonic Acid → 3-Quinolineacrylic acid

HRID 1873755Notes

Reaction equation

HRID 1873755 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1>N1C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[CH:14][C:15]([OH:17])=[O:16])[CH:2]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 836413-Quinolinecarboxaldehyde

Product 1

HCID 14722903-Quinolineacrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.006 g (6.4 mmol) of quinoline-3-carbaldehyde were dissolved in 10 ml of pyridine and 0.794 g (7.6 mmol) of malonic acid and 54 mg (0.6 mmol) of piperidine were added. The resulting solution was boiled under reflux for 6 h. The solution was allowed to cool to room temperature and kept for 16 h whereupon the product precipitated. The product was isolated by filtration. Yield: 0.765 g.

Workup

  1. temperatureunder reflux for 6 h
  2. customprecipitated
  3. customThe product was isolated by filtration

Sources & evidence

ORD record
ord-567cedf69fa94de6944086f40c7f7697
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Reaction notes

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