Sodium Hydroxide → 5H-Indeno(1,2-b)pyridin-5-one

HRID 1093029

Reaktionsgleichung

Reaktionsgleichung von HRID 1093029
[OH-].[Na+].[N:3]1[C:16]2[C:7](=C3[C:13](=[CH:14][CH:15]=2)[CH:12]=[CH:11][C:10](=O)[C:9]3=[O:18])[CH:6]=[CH:5][CH:4]=1>>[CH:6]1[C:7]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]=2[N:3]=[CH:4][CH:5]=1

Komponenten

3

Edukt 2

HCID 14798Sodium HydroxideHCID 199224561-Azaphenanthrene-5,6-dione

Produkt 1

HCID 774895H-Indeno(1,2-b)pyridin-5-oneAusbeute 38 %

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Subsequently, in a stream of argon, 1.5 L of a 10% aqueous solution of sodium hydroxide was added to 51.0 g (244 mmol) of 1-azaphenanthrene-5,6-dione, and heated and stirred at 85° C. for 90 minutes. After the mixture was cooled to room temperature, the precipitate was filtered out. The filtrate was extracted with chloroform and concentrated, and added to the precipitate, whereby a crude material was obtained. The crude material was purified by chromatography on silica gel with toluene/ethyl acetate=10:1 to give 16.8 g of 4-azafluorene-9-one (37.9% yield).

Aufarbeitung

  1. temperatureheated
  2. temperatureAfter the mixture was cooled to room temperature
  3. filtrationthe precipitate was filtered out
  4. extractionThe filtrate was extracted with chloroform
  5. concentrationconcentrated
  6. additionadded to the precipitate, whereby a crude material
  7. customwas obtained
  8. customThe crude material was purified by chromatography on silica gel with toluene/ethyl acetate=10:1

Quellen und Nachweise

ORD-Eintrag
ord-6a7b1117398e4e65b484f3b7d4a81c71
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129899B1

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