Aluminum(III) Chloride → 3-Cyano-7-hydroxyquinoline

HRID 454188Notes

Reaction equation

HRID 454188 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([O:13]C)[CH:7]=2)#[N:2].[Cl-].[Cl-].[Cl-].[Al+3]>C1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([OH:13])[CH:7]=2)#[N:2]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 154022003-Cyano-7-methoxyquinoline

Product 1

HCID 1357631173-Cyano-7-hydroxyquinolineYield 68%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Cyano-7-methoxyquinoline (380 mg, 2.1 mmol) was suspended in benzene (10 ml), aluminium trichloride (826 mg, 6.2 mmol) was added and the mixture heated at reflux for 30 minutes. More aluminium trichloride (275 mg, 2.1 mmol) was added and the mixture refluxed for a further 2 hours. The solvent was evaporated, the dark green solid was added to ice and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and evaporated. The solid was found to contain some aluminium salts which were removed as follows. The solid was dissolved in dichloromethane (200 ml) was stirred vigorously with a saturated sodium hydrogen carbonate solution for 1 hour. The product was collected by filtration of the aqueous phase and dried over phosphorus pentoxide under vacuum to give 3-cyano-7-hydroxyquinoline (238 mg, 68%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 30 minutes
  3. temperaturethe mixture refluxed for a further 2 hours
  4. customThe solvent was evaporated
  5. additionthe dark green solid was added to ice
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customwere removed
  11. dissolutionThe solid was dissolved in dichloromethane (200 ml)
  12. filtrationThe product was collected by filtration of the aqueous phase
  13. dry with materialdried over phosphorus pentoxide under vacuum

Sources & evidence

ORD record
ord-037157e5b68641cbb95dd3f54fa3d9d9
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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