Diethylene Glycol → Azafluorene

HRID 1463681Notes

Reaction equation

HRID 1463681 reaction equation
[N:1]1[C:13]2[C:12](=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.NN.C(O)COCCO.C(O)C(O)C(O)C(O)C(O)C=O.[O-]S([O-])(=O)=O.[Mg+2]>CCCCCC>[N:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 9321HydrazineHCID 426139H-Indeno(2,1-b)pyridin-9-oneHCID 21924827Magnesium;2,3,4,5,6-pentahydroxyhexanal;sulfate

Product 1

HCID 12226515AzafluoreneYield 66.6%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4.6 g (25.4 mmole) of 1-azafluoren-9-one was added to a solution of 9 ml (0.28 mole) of hydrazine and 50 ml of diethyleneglycol. Heating was started and the temperature was kept at 100° for 15 minutes, then raised to 195° and kept there for 1 hr. TLC showed the reaction was complete. The reaction solution was cooled to below 100° and poured into 300 ml of ice water. The aqueous phase was saturated with salt and extracted with 8×100 ml ether. The ether was dried with sodium sulfate and evaporated to yield 3.73 g of crude product. This was dissolved in hexane and treated with Magnesol, filtered and evaporated and finally recrystallized from hexane to yield 2.83 g of pure 1-azafluorene.

Workup

  1. temperatureHeating
  2. temperatureraised to 195°
  3. waitkept there for 1 hr
  4. temperatureThe reaction solution was cooled to below 100°
  5. extractionextracted with 8×100 ml ether
  6. dry with materialThe ether was dried with sodium sulfate
  7. customevaporated
  8. customto yield 3.73 g of crude product
  9. filtrationfiltered
  10. customevaporated
  11. customfinally recrystallized from hexane

Sources & evidence

ORD record
ord-2c90c633afb64ef791319d40d0c74bd2
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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