Methyl 3-methyl-1-oxidopyridin-4-yl ether → 4-Methoxy-3-methylpyridine

HRID 6889Notes

Reaction equation

HRID 6889 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]>[Pd].CO>[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 1

HCID 817250Methyl 3-methyl-1-oxidopyridin-4-yl ether

Product 1

HCID 47377664-Methoxy-3-methylpyridineYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4 g (28.8 mmol) 3-methyl-4-methoxy pyridine N-oxide (prepared according to the method described in Kohl, Bernhard et al; J. Med. Chem.; 1992; 1049–1057) and 1.1 mg of 5% palladium on charcoal in 50 ml of methanol is hydrogenated at 20 atms at room temperature for 12 hours (2*6 hours). Filtration through celite, and evaporation gave 3,2 g (90%) of a light green oil.

Workup

  1. customprepared
  2. custom(2*6 hours)
  3. filtrationFiltration
  4. customthrough celite, and evaporation

Sources & evidence

ORD record
ord-a333f75678774bb6bf82775dc7ec01b8
Source dataset
uspto-grants-2006_08
Patent number
US07084163B2

Reaction notes

Loading…