Malonic Acid → HCID 12854456, compound

HRID 2166878Notes

Reaction equation

HRID 2166878 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]([CH:13]=O)=[CH:3]1.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18]>N1C=CC=CC=1.N1CCCCC1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4](/[CH:13]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:3]1

Participants

5

Reactant 2

HCID 867Malonic AcidHCID 12854441HCID 12854441, compound

Product 1

HCID 12854456HCID 12854456, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 1-methyl-3-formyl-4(1H)-quinolone (5.61 g) and malonic acid (4.5 g) in pyridine (45 ml) with 3 drops piperidine was heated on a steam-bath for two hours. The pyridine was removed in vacuo and the solid residue washed with water and dried. Recrystallisation from DMF/H2O gave the title compound. NMR confirmed the structure as pure trans-isomer, m.p. 248°-250° (with decomposition).

Workup

  1. temperaturewas heated on a steam-bath for two hours
  2. customThe pyridine was removed in vacuo
  3. washthe solid residue washed with water
  4. customdried
  5. customRecrystallisation from DMF/H2O

Sources & evidence

ORD record
ord-d69945822dcb42849e7094eb4cf917b2
Source dataset
uspto-grants-1983_06
Patent number
US04390541

Reaction notes

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