HCID 21252829, compound → HCID 21252814, compound

HRID 850808Notes

Reaction equation

HRID 850808 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[CH:7]=[CH:6][C:5]2=[O:19]>C(O)(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:9]3=[C:4]([C:5](=[O:19])[CH:6]=[CH:7][N:8]3[C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]2=3)[CH:3]=1

Participants

4

Reactant 1

HCID 21252829HCID 21252829, compound

Product 1

HCID 21252814HCID 21252814, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

6-chloro-1-(4-chlorophenyl)-4(1H)-quinolinone (2 g) obtained in step 4 was dissolved in acetic acid (150 ml) and to the solution were added a boron tribromide-acetic acid complex (44 ml) and palladium diacetate (6.28 g). The mixture was heated under reflux for 1 hour in an argon atmosphere and allowed to cool. The insoluble content was removed by filtration and the solution was extracted with water and ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=1:2) to obtain the title compound (40 mg, 2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour in an argon atmosphere
  3. temperatureto cool
  4. customThe insoluble content was removed by filtration
  5. extractionthe solution was extracted with water and ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=1:2)

Sources & evidence

ORD record
ord-285712732b6e4d89bf68867c8a37b76d
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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