Hydrogen Peroxide → 3-Methoxy-2-methylpyridine 1-oxide

HRID 845541

Reaction equation

HRID 845541 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[OH:10]O>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:9])=[N+:5]([O-:10])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 30152703-Methoxy-2-methylpyridine

Product 1

HCID 122140163-Methoxy-2-methylpyridine 1-oxideYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

15.3 g (0.124 mole) of 3-methoxy-2-methylpyridine are dissolved in 100 ml of glacial acetic acid, and 40 ml of 30% strength hydrogen peroxide are added in 4 portions at 80° C. in the course of 6 hours. The mixture is stirred for a further three hours and then concentrated in vacuo (1.5 kPa), and two 50 ml portions of acetic acid are added, the mixture being concentrated completely after each addition. Following negative detection of per-compounds, the mixture is distilled in a bulb tube oven. The fraction which distills at 120° C. (1.5 Pa) is extracted by stirring in a little diethyl ether and the solid is filtered off and dried. 12 g (60% of theory) of 3-methoxy-2-methylpyridine 1-oxide are obtained in the form of colorless crystals of m.p. 72°-78° C.

Workup

  1. concentrationconcentrated in vacuo (1.5 kPa), and two 50 ml portions of acetic acid
  2. additionare added
  3. concentrationthe mixture being concentrated completely
  4. additionafter each addition
  5. distillationthe mixture is distilled in a bulb tube oven
  6. distillationThe fraction which distills at 120° C. (1.5 Pa)
  7. extractionis extracted
  8. stirringby stirring in a little diethyl ether
  9. filtrationthe solid is filtered off
  10. customdried

Sources & evidence

ORD record
ord-3c8d6b5193b74c0c803784307d37c20c
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Linked notes

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