Acetic Acid → 3-Methoxy-2-methylpyridine 1-oxide

HRID 398252

Reaction equation

HRID 398252 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.C(O)(=[O:12])C.OO.C(=O)([O-])[O-].[Na+].[Na+].[K+].[Br-]>O>[CH3:1][O:2][C:3]1[C:4]([CH3:9])=[N+:5]([O-:12])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 253877Potassium BromideHCID 30152703-Methoxy-2-methylpyridine

Product 1

HCID 122140163-Methoxy-2-methylpyridine 1-oxideYield 16.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution obtained by dissolving 3-methoxy-2-methylpyridine (14.8 g, 0.12 mol) in acetic acid (44 g, 0.12×2.5 mol) was added 31% hydrogen peroxide (33 g, 0.12×2.5 mol), followed by stirring in an oil bath at 100° C. for 16 hours. The reaction solution was then cooled and poured into iced-water. To the mixture was then added sodium carbonate (solid) so as to be weak alkalinity. The resultant solution was extracted with ethyl acetate to obtain 1.45 g (percent yield: 16.7%) of 3-methoxy-2-methylpyridine-N-oxide IR KBr cm−1: 1668, 1647, 1584, 1503, 1302, 1266, 1188, 1128, 792. 1H-NMR (60 MHz, CDCl3, δ): 2.4 (3R, s, CH3), 3.8 (3H, s, OCH3), 6.5-7.2 (2H, m, pyridine ring H×2), 7.7-8.0 (1H, m, pyridine ring H).

Workup

  1. customTo a solution obtained
  2. temperatureThe reaction solution was then cooled
  3. extractionThe resultant solution was extracted with ethyl acetate

Sources & evidence

ORD record
ord-dde7fcb5f8cf429d9beeef8755c09d37
Source dataset
uspto-grants-2003_08
Patent number
US06610853B1

Linked notes

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