Aluminum(III) Chloride → HCID 57567489, compound

HRID 1727851Notes

Reaction equation

HRID 1727851 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[F:25].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH2:1]([O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[F:25])[C:32]1[CH:31]=[CH:30][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 114507634-(2-Fluoro-4-nitrophenoxy)-6,7-dimethoxyquinolineHCID 21226206Ethyl acetate hexane

Product 1

HCID 57567489HCID 57567489, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluoro-nitrobenzene (4.3 g) was dissolved in chloroform (200 ml) to prepare a solution. Aluminium chloride (10 g) was added to the solution, and the mixture was heated under reflux for 2 hr. The solvent was removed by evaporation before water (200 ml) was carefully added to the residue. The precipitated crude crystal (6.5 g) was collected by filtration. This crude crystal was dissolved in dimethylformamide (150 ml). Potassium carbonate (9.0 g) and benzyl chloride (4.5 g) were added to the solution, and the mixture was stirred at room temperature for 5 hr. The mixture was extracted with ethyl acetate. The extract was then washed with saturated brine and was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under the reduced pressure. The residue was purified by column chromatography on silica gel, and the title compound (1.4 g, yield 27%) was obtained from the fraction of n-hexane:ethyl acetate (1:4).

Workup

  1. customto prepare a solution
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hr
  4. customThe solvent was removed by evaporation before water (200 ml)
  5. additionwas carefully added to the residue
  6. customThe precipitated crude crystal (6.5 g)
  7. filtrationwas collected by filtration
  8. dissolutionThis crude crystal was dissolved in dimethylformamide (150 ml)
  9. additionPotassium carbonate (9.0 g) and benzyl chloride (4.5 g) were added to the solution
  10. extractionThe mixture was extracted with ethyl acetate
  11. washThe extract was then washed with saturated brine
  12. dry with materialwas dried over anhydrous sodium sulfate
  13. customthe solvent was removed by evaporation under the reduced pressure
  14. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f1c4cac7f8ec44b195894e5603e5cfcc
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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