8-Hydroxyquinoline → Aluminium tri(quinolin-8-olate)

HRID 279399

Reaction equation

HRID 279399 reaction equation
C([O-])(=O)CCCCCCCCCCCCCCCCC.[Al+3:21].C([O-])(=O)CCCCCCCCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCCCCCCCC.[OH:62][C:63]1[CH:64]=[CH:65][CH:66]=[C:67]2[C:72]=1[N:71]=[CH:70][CH:69]=[CH:68]2>C1(C)C=CC=CC=1>[CH:65]1[CH:64]=[C:63]([O-:62])[C:72]2[N:71]=[CH:70][CH:69]=[CH:68][C:67]=2[CH:66]=1.[CH:65]1[CH:64]=[C:63]([O-:62])[C:72]2[N:71]=[CH:70][CH:69]=[CH:68][C:67]=2[CH:66]=1.[CH:65]1[CH:64]=[C:63]([O-:62])[C:72]2[N:71]=[CH:70][CH:69]=[CH:68][C:67]=2[CH:66]=1.[Al+3:21]

Participants

4

Reactant 2

HCID 19238-HydroxyquinolineHCID 12496Aluminum Stearate

Product 1

HCID 90594Aluminium tri(quinolin-8-olate)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Aluminum stearate, Al[CH3(CH2)16CO2]3, (10.0 g, Fisher Scientific Co., Pittsburgh, Pa., technical grade) was placed in a 250 mL round bottomed flask equipped with a magnetic stir bar and a reflux condenser. Toluene (50 mL) was added to give a white slurry. Separately, a 6.0 g sample of 8-hydroxyquinoline (41.3 mmol) was dissolved in 150 mL of toluene and the solution was gravity filtered through a coarse glass frit into the reaction flask. This removed an insoluble minor impurity found in the 8-hydroxyquinoline. After the addition of the 8-hydroxyquinoline to the aluminum stearate-toluene solution, the reaction flask was heated to reflux by means of an electric heating mantle. As the reaction warmed, but prior to refluxing, a large quantity of a fine yellow solid precipitated. The reaction mixture was refluxed for approximately 72 hours, cooled, and filtered. The yellow filter cake was washed sequentially with two 50 mL portions of toluene and two 50 mL portions of petroleum ether. After vacuum drying, the filter cake provided 5.4 g of tris(8-quinolinolato)aluminum as fine yellow needles. An 1H-NMR of the product precipitated from the toluene reaction mixture showed no significant resonances other than those of the desired product.

Workup

  1. customequipped with a magnetic stir bar and a reflux condenser
  2. customto give a white slurry
  3. filtrationfiltered through a coarse glass frit into the reaction flask
  4. customThis removed an insoluble minor impurity
  5. additionAfter the addition of the 8-hydroxyquinoline to the aluminum stearate-toluene solution
  6. temperaturethe reaction flask was heated
  7. temperatureto reflux by means of an electric heating mantle
  8. temperatureAs the reaction warmed
  9. temperatureto refluxing
  10. customa large quantity of a fine yellow solid precipitated
  11. temperatureThe reaction mixture was refluxed for approximately 72 hours
  12. temperaturecooled
  13. filtrationfiltered
  14. washThe yellow filter cake was washed sequentially with two 50 mL portions of toluene and two 50 mL portions of petroleum ether
  15. customAfter vacuum drying

Sources & evidence

ORD record
ord-92d5daa74753410283ff95efb4551314
Source dataset
uspto-grants-2002_03
Patent number
US06362339B1

Linked notes

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