Diethylene Glycol → Azafluorene

HRID 1648152Notes

Reaction equation

HRID 1648152 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-f937471d2f134a0aaa388176d5a3b2cb
Source dataset
uspto-grants-1995_07
Patent number
US05434264

Reaction notes

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