Hydrogen Peroxide → Methyl 3-hydroxyquinoline-8-carboxylate

HRID 2427231Notes

Reaction equation

HRID 2427231 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:4].OO.C([O-])(O)=[O:18].[Na+]>CC(O)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([OH:18])=[CH:10]2)=[O:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 12554533Methyl Quinoline-8-Carboxylate

Product 1

HCID 57440941Methyl 3-hydroxyquinoline-8-carboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the intermediate 8-Quinolinecarboxylic acid methyl ester (2.89 mmol) in AcOH (4 ml) was added 30% H2O2 (0.6 ml). The reaction mixture was heated at 85 degrees for 7.5 hr. The reaction mixture was treated with sat NaHCO3, and extracted six times with CHCl3. Organic layer was dried over anhydrous MgSO4, and concentrated. Crude residue was triturated with CHCl3/Toluene to provide compound 313 (256 mg, 44%, in 2 steps).

Workup

  1. temperatureThe reaction mixture was heated at 85 degrees for 7.5 hr
  2. extractionextracted six times with CHCl3
  3. dry with materialOrganic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customCrude residue was triturated with CHCl3/Toluene

Sources & evidence

ORD record
ord-61de199e912b421584419b8a20715c67
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

Loading…