Hydrogen Peroxide → Methyl 3-hydroxyquinoline-8-carboxylate

HRID 1370490Notes

Reaction equation

HRID 1370490 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

Conditions

Temperature
85 °C

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° C. for 7.5 h. 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 97 (256 mg, 44%, in 2 steps).

Workup

  1. extractionextracted six times with CHCl3
  2. dry with materialOrganic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customCrude residue was triturated with CHCl3/toluene

Sources & evidence

ORD record
ord-a16cd3df5e3946e2804bb48e9e3334ca
Source dataset
uspto-grants-2003_06
Patent number
US06583157B2

Reaction notes

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