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

HRID 1640030Notes

Reaction equation

HRID 1640030 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
85 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f976bade2bde4492bfe8668304648912
Source dataset
uspto-grants-2012_02
Patent number
US08110685B2

Reaction notes

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