Aluminum(III) Chloride → 4-Chloro-7-hydroxycinnoline

HRID 1057359Notes

Reaction equation

HRID 1057359 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Cl:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16]C)=[CH:13][CH:14]=2)[N:9]=[N:8][CH:7]=1>C1C=CC=CC=1>[Cl:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=2)[N:9]=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 219910214-Chloro-7-methoxycinnoline

Product 1

HCID 1360879794-Chloro-7-hydroxycinnolineYield 53.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Aluminium trichloride (2.6 g, 19 mmol) was added in portions to a suspension of 4-chloro-7-methoxycinnoline (0.9 g, 3.8 mmol), (J. Chem. Soc. 1955, 2100), in benzene (15 ml) and the mixture was heated at reflux for 1 hour. The solvent was removed by evaporation and the residue was partitioned between ice/water and ethyl acetate. Aqueous saturated sodium chloride solution was added and the organic layer was separated. The organic layer was washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether, collected, filtered and dried under vacuum to give 4-chloro-7-hydroxycinnoline (368 mg, 53%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was removed by evaporation
  4. customthe residue was partitioned between ice/water and ethyl acetate
  5. additionAqueous saturated sodium chloride solution was added
  6. customthe organic layer was separated
  7. washThe organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed by evaporation
  10. customThe residue was triturated with ether
  11. customcollected
  12. filtrationfiltered
  13. customdried under vacuum

Sources & evidence

ORD record
ord-0a1938fefa664f89ada3a81d4435ff05
Source dataset
uspto-grants-2003_02
Patent number
US06514971B1

Reaction notes

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