8-Hydroxyquinoline → HCID 178478625, compound

HRID 1979026Notes

Reaction equation

HRID 1979026 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].N1C2C(=CC=CC=2)C=CC=1O>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

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 24193Titanium TetrachlorideHCID 178515546HCID 178515546, compound

Product 1

HCID 178478625HCID 178478625, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The reaction is performed under an atmosphere of dry nitrogen. 8-Quinolinol powder (1.45 g, 10.0 mmol) is added to a flask and is stirred at room temperature for 10 min. Heptane (100 mL) is added, and the mixture is stirred at 40° C. for 30 min. The stirring rate is adjusted to prevent solids from depositing on the walls of the flask. Titanium tetrachloride (10 mL of 1.0 M solution in heptane) is added dropwise to the quinolinol, and the reaction mixture is stirred at room temperature for 20 h at a rate effective to prevent solids from depositing on the walls of the flask. The color changes from white to tomato-juice red. The solids are isolated by decanting the liquid portion. Residual solvent is removed from the solids using vacuum and a nitrogen purge for 30 min. The flask containing the red, solid product, 8-quinolinoxytitanium trichloride (3.04 g), is transferred to a dry box. For comparison purposes, a sample of this material is tested in the ethylene polymerization described in Example 6. The results are reported in Table 1 for Example “C1.”

Workup

  1. stirringthe mixture is stirred at 40° C. for 30 min
  2. stirringthe reaction mixture is stirred at room temperature for 20 h at a rate effective
  3. customThe solids are isolated
  4. customby decanting the liquid portion
  5. customResidual solvent is removed from the solids
  6. customa nitrogen purge for 30 min
  7. additionThe flask containing the red, solid product, 8-quinolinoxytitanium trichloride (3.04 g)
  8. customis transferred to a dry box
  9. customFor comparison purposes, a sample of this material is tested in the ethylene polymerization

Sources & evidence

ORD record
ord-adfb9b92d3c54e768cb1bb9de038bc50
Source dataset
uspto-grants-2001_05
Patent number
US06239239B1

Reaction notes

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