5-Chloro-8-hydroxyquinoline → Quinoline

HRID 1766594Notes

Reaction equation

HRID 1766594 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 Pd2 DBA3, 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-8a027fcb7f0b43e2a0903c63d03738c0
Source dataset
uspto-grants-2007_06
Patent number
US07230107B1

Reaction notes

Loading…