8-Hydroxyquinoline → HCID 178478625, compound

HRID 376489Notes

Reaction equation

HRID 376489 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][CH:2]=1.[Ti:12](Cl)(Cl)(Cl)[Cl:13]>CCCCCCC>[Cl-:13].[Cl-:13].[Cl-:13].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][Ti+3:12])[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 19238-HydroxyquinolineHCID 24193Titanium Tetrachloride

Product 1

HCID 178478625HCID 178478625, compoundYield 286.6%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
32.5 °C

Procedure

8-Quinolinol (1.45 g, 0.010 mol) is added to a three-neck flask with heptane (30 mL), and the mixture is stirred under nitrogen at 25 to 40° C. for 0.5 h. It becomes a pale yellow suspension. Titanium tetrachloride (10 mL of 1.0 M solution in heptane, 0.010 mol) is added dropwise to the suspension. After stirring at 25° C. for 2 h, solvents are removed under vacuum. The product is washed with heptane (30 mL), and the washings are decanted. The residue is dried under vacuum for 1 h, and is then recrystallized from a mixture of hydrocarbon solvents to give purple crystals of 8-quinolinoxytitanium trichloride (2.85 g, 95%).

Workup

  1. stirringAfter stirring at 25° C. for 2 h
  2. customsolvents are removed under vacuum
  3. washThe product is washed with heptane (30 mL)
  4. customthe washings are decanted
  5. customThe residue is dried under vacuum for 1 h
  6. customis then recrystallized from a mixture of hydrocarbon solvents

Sources & evidence

ORD record
ord-ac385d0854dd4edf8cfe1c06c2b7e951
Source dataset
uspto-grants-2000_02
Patent number
US06020493

Reaction notes

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