Hydrogen Peroxide → Methyl 4-(1-oxidopyridin-3-yl)benzoate

HRID 910613Notes

Reaction equation

HRID 910613 reaction equation
[OH:1]O.[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH:4]=1>C(O)(=O)C>[O-:1][N+:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 4133187Methyl 4-pyridin-3-ylbenzoate

Product 1

HCID 18182583Methyl 4-(1-oxidopyridin-3-yl)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Acetic acid (10 mL) and aqueous 30% hydrogen peroxide (452 μL) were added to methyl 4-pyridin-3-ylbenzoate (708 mg), followed by stirring at 70° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, an aqueous saturated sodium hydrogencarbonate solution was added, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methanol/chloroform=0% to 10%) to obtain methyl 4-(1-oxidopyridin-3-yl)benzoate (720 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionan aqueous saturated sodium hydrogencarbonate solution was added
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (methanol/chloroform=0% to 10%)

Sources & evidence

ORD record
ord-d0ad7d63b1ac43b981c9c355e4e1bca9
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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