Diethyl Carbonate → HCID 20375644, Verbindung

HRID 1390282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1390282
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[CH:3]=1.[H-].[Na+].[C:21](=[O:28])([O:25][CH2:26][CH3:27])OCC>O>[O:18]=[C:4]1[CH:3]=[C:2]([CH:1]([C:21]([O:25][CH2:26][CH3:27])=[O:28])[C:21]([O:25][CH2:26][CH3:27])=[O:28])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 2691834-Methyl-1-phenyl-2(1H)-quinolone

Produkt 1

HCID 20375644HCID 20375644, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1,2-dihydro-4-methyl-2-oxo-1-phenylquinoline (4.7 g.), sodium hydride (4.8 g., 60% w/w dispersion in oil, washed as in Example 1) and diethyl carbonate (50 ml.) was stirred under reflux for 2 hours. Any excess of sodium hydride was then destroyed by addition of methanol to the cooled suspension, and the mixture was then poured into ether (1 l.). The yellow precipitate was collected by filtration, and washed with ether (200 ml.). It was suspended in ethanol (50 ml.), concentrated hydrochloric acid was added to give a pH of 3, and the resultant solution was poured into water (200 ml.). The precipitate was extracted into ether, and the combined extracts were washed with water, dried over magnesium sulphate, and evaporated in vacuo. A sample of the residual solid was recrystallised from a mixture of benzene and cyclohexane to give diethyl 1,2-dihydro-2-oxo-1-phenylquinol-4-ylmalonate, m.p. 101-103° C.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. customAny excess of sodium hydride was then destroyed by addition of methanol to the cooled suspension
  3. additionthe mixture was then poured into ether (1 l.)
  4. filtrationThe yellow precipitate was collected by filtration
  5. washwashed with ether (200 ml.)
  6. additionconcentrated hydrochloric acid was added
  7. customto give a pH of 3
  8. extractionThe precipitate was extracted into ether
  9. washthe combined extracts were washed with water
  10. dry with materialdried over magnesium sulphate
  11. customevaporated in vacuo
  12. customA sample of the residual solid was recrystallised from a mixture of benzene and cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-1d4945aa43984ff59da1316ae4ac41c4
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04138490

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