Acetic Acid → 2-Acetoxy-8-hydroxyquinoline

HRID 1167191Notes

Reaction equation

HRID 1167191 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N+:10]([O-])=[CH:9][CH:8]=[CH:7]2.[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14].C(O)(=O)C>C1(C)C=CC=CC=1>[C:13]([O:16][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 7918Acetic AnhydrideHCID 143128-Hydroxyquinoline N-oxide

Product 1

HCID 229959082-Acetoxy-8-hydroxyquinolineYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
135 °C

Procedure

64 g (397 mmol) of 8-hydroxyquinoline N-oxide, 550 ml of acetic anhydride and 40 ml of acetic acid are placed in a 1 l round-bottomed flask. The reaction mixture is heated at reflux (135° C.) for 24 h, 40 ml of acetic acid are then again added and heating is continued for 1 h 30. The reaction mixture is allowed to return to ambient temperature and 400 ml of toluene are added. A precipitate appears and is filtered off. A further 400 ml of toluene are added and filtration is carried out. The precipitate is washed with 200 ml of ethyl ether and is dried in a desiccator under vacuum over phosphorus pentoxide to provide to provide 70.5 g of 2-acetoxy-8-hydroxyquinoline in the form of a brown solid. (Yield: 88%)

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureheating
  3. customto return to ambient temperature
  4. filtrationis filtered off
  5. additionA further 400 ml of toluene are added
  6. filtrationfiltration
  7. washThe precipitate is washed with 200 ml of ethyl ether
  8. dry with materialis dried in a desiccator under vacuum over phosphorus pentoxide
  9. customto provide

Sources & evidence

ORD record
ord-b28ae0cf873d4cd6a9dd97283cc7c71a
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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