Hydrogen Peroxide → Pyridine, 3-methoxy-, 1-oxide

HRID 2378452Notes

Reaction equation

HRID 2378452 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[OH:9]O>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[N+:5]([O-:9])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 237193-Methoxypyridine

Product 1

HCID 139850Pyridine, 3-methoxy-, 1-oxideYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

3-Methoxypyridine (20.08 g, 209 mmol) was dissolved in 100 mL of acetic acid. 30% H2O2 (28.3 mL, 275 mmol) was added and the reaction mixture was heated at 70° C. for six h. The cooled reaction mixture was concentrated and the residue dissolved in CH2Cl2 and stirred overnight with 20 g of solid potassium carbonate. The mixture was filtered and concentrated to give compound 762A (25.2 g, 100%) as a light yellow solid which was characterized by 1H NMR and carried on to the next step.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated
  3. dissolutionthe residue dissolved in CH2Cl2
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b70bdb761c74664ae87a4f6e426d3f6
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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