Diethyl Malonate → Ethyl 1-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 2269620

Reaktionsgleichung

Reaktionsgleichung von HRID 2269620
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5]CC)=O.[H-].[Na+].[H][H].[CH2:16]([N:23]1[C:29](=O)[O:28]C(=O)[C:25]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:24]12)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:23]1[C:24]2[C:25](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:3]([OH:5])=[C:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:29]1=[O:28])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 520756N-Benzylisatoic anhydrideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 54711837Ethyl 1-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylateAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a solution of 4.50 g of diethyl malonate in 20 ml of N,N-dimethylformamide was gradually added 1.10 g of 62.4% sodium hydride at room temperature, and stirring was continued at room temperature until hydrogen evolution ceased. The reaction solution was heated to 80° C., and a solution of 6.70 g of N-benzylisatoic anhydride in 20 ml of N,N-dimethylformamide was added dropwise. After the addition, the reaction mixture was stirred under heating at 120° C. for 7 hours. After cooling to room temperature, the reaction mixture was poured into ice water and washed with ethyl acetate. The aqueous phase was made acidic with 1 N hydrochloric acid, and extracted with ethyl acetate. The organic phase was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was crystallized from ethanol to give 5.88 g of ethyl 1-benzyl-4-hydroxy-1,2-dihydro-2-oxoquinoline-3-carboxylate.

Aufarbeitung

  1. customat room temperature
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred
  4. temperatureunder heating at 120° C. for 7 hours
  5. temperatureAfter cooling to room temperature
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. washThe organic phase was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customAfter removal of the drying agent
  11. filtrationby filtration
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customThe residue was crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-7ea00b8b48ac4a6e87e7014f410351f6
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329525B1

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