8-Hydroxyquinoline → HCID 178524122, compound

HRID 493890Notes

Reaction equation

HRID 493890 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Ir:12](Cl)(Cl)Cl.[C:16]1([C:22]2[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:31](=[O:34])([O-:33])[O-:32].[Na+].[Na+]>C(OCCO)C>[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:31]([O-:33])=[O:32])[CH:8]=[CH:7]2.[Ir+3:12].[C:16]1([C:22]2[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1.[C:16]1([C:22]2[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1.[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:31]([O-:32])=[O:34])[CH:8]=[CH:7]2.[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:31]([O-:33])=[O:32])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 10340Sodium CarbonateHCID 86584703HCID 86584703, compound

Product 1

HCID 178524122HCID 178524122, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

4.7 mmol (0.68 g) of 8-hydroxyquinoline was added to a room-temperature solution of 0.14 mmol 2-phenylbenzothiazole Iridium chloride dimer (0.19 g) in 20 mL of 2-ethoxyethanol. Approximately 700 mg of sodium carbonate was added, and the mixture was heated to reflux under nitrogen in an oil bath overnight (23 hrs.). Reaction mixture was cooled to room temperature, and the red precipitate was filtered off via vacuum. The filtrate was concentrated and methanol was added to precipitate more product. Successive filtrations and precipitations afforded a 57% yield. The emission spectrum is in FIG. 43 and the proton NMR spectrum is in FIG. 44.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under nitrogen in an oil bath overnight (23 hrs.)
  3. customReaction mixture
  4. filtrationthe red precipitate was filtered off via vacuum
  5. concentrationThe filtrate was concentrated
  6. additionmethanol was added
  7. customto precipitate more product
  8. filtrationSuccessive filtrations and precipitations
  9. customafforded a 57% yield

Sources & evidence

ORD record
ord-f2e8860e6185437880139aafc2cd18d4
Source dataset
uspto-grants-2009_05
Patent number
US07537844B2

Reaction notes

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