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

HRID 910613

Reaktionsgleichung

Reaktionsgleichung von HRID 910613
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-d0ad7d63b1ac43b981c9c355e4e1bca9
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022208B2

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