5-Chloro-8-hydroxyquinoline → Quinoline

HRID 1174434Notes

Reaction equation

HRID 1174434 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9](O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C1(NC2C=CC=CC=2)C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1.C1(C)C=CC=CC=1>[N:7]1[C:8]2[C:3](=[CH:2][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 28175-Chloro-8-hydroxyquinolineHCID 11487DiphenylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 21840791Dioxane tolueneSolvent

Procedure

8.98 g, 0.05 mol of 5-chloro-8-hydroxyquinoline (Aldrich), 10.15 g, 0.06 mol of diphenylamine, 350 mL of 1:1 dioxane/toluene, 0.917 g, 0.001 mol Pd2DBA3, 0.4350 g, 0.0021 mol of tri-t-butylphosphine, and 18.42 g, 0.11 mol lithium bis(trimethylsilyl)amide were combined and refluxed together for a total of 180 hrs. The mixture was cooled to room temperature and filtered through celite with dichloromethane rinses. The mixture was partially evaporated and the organic layer was washed with 1N HCl then neutralized to pH 8 with saturated sodium bicarbonate. The organic layer was then dried with Na2SO4, filtered and concentrated by rotary evaporation. The product was purified by silica column chromatography using dichloromethane eluent. Yield 11.13 g of a bright yellow solid.

Workup

  1. temperaturerefluxed together for a total of 180 hrs
  2. filtrationfiltered through celite with dichloromethane rinses
  3. customThe mixture was partially evaporated
  4. washthe organic layer was washed with 1N HCl
  5. dry with materialThe organic layer was then dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe product was purified by silica column chromatography

Sources & evidence

ORD record
ord-2c60f750a7324fc2be3f0b8dda5bbd13
Source dataset
uspto-grants-2010_11
Patent number
US07838127B1

Reaction notes

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