Sodium Chloride → 4-Azafluorene

HRID 1093030

Reaction equation

HRID 1093030 reaction equation
[CH: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[N:4]=[CH:3][CH:2]=1.O.NN.[Cl-].[Na+]>C(O)COCCO>[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[N:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 774895H-Indeno(1,2-b)pyridin-5-one

Product 1

HCID 92054-AzafluoreneYield 99%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
168 °C

Procedure

Subsequently, in a stream of argon, 500 mL of diethylene glycol was added to 16.8 g (92.6 mmol) of 4-azafluorene-9-one and 25 mL (370 mmol) of hydrazine monohydrate, and was heated and stirred at 168° C. for 3 hours. After the reaction liquid was cooled to room temperature, an aqueous solution of sodium chloride was added to the reaction liquid, and then, was extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate and concentrated, to thereby obtain 15.3 g of 4-azafluorene (99% yield).

Workup

  1. temperaturewas heated
  2. customAfter the reaction liquid
  3. temperaturewas cooled to room temperature
  4. extractionwas extracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e5ea128c0996488d818612d85c2ddd28
Source dataset
uspto-grants-2012_03
Patent number
US08129899B1

Linked notes

Loading…