2,3-Dimethyl-4-nitropyridine-N-oxide → Pyridine, 4-methoxy-2,3-dimethyl-, 1-oxide

HRID 2073958Notes

Reaction equation

HRID 2073958 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N+:3]=1[O-:12].[C:13](=O)([O-])[OH:14].[K+]>CO.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:14][CH3:13])[CH:5]=[CH:4][N+:3]=1[O-:12]

Participants

5

Reactant 2

HCID 1482232,3-Dimethyl-4-nitropyridine-N-oxideHCID 516893Potassium Bicarbonate

Product 1

HCID 10630707Pyridine, 4-methoxy-2,3-dimethyl-, 1-oxideYield 94.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 887MethanolSolvent

Procedure

2,3-Dimethyl-4-nitropyridine-1-oxide (5 g) was dissolved in methanol (30 ml). To the solution were added tetrabutylammonium bromide (0.5 g) and potassium hydrogen carbonate (5.6 g), and the mixture was heated (temperature 80°-85° C.) under reflux with stirring for 10 hours. The solid matter was removed from the reaction mixture by filtration, and the filtrate was concentrated and applied to a silica gel (100 g) column. Elution with methanol-dichloromethane (1:9) and recrystallization from ethyl acetate-hexane gave 4.3 g of white 2,3-dimethyl-4-methoxypyridine-1-oxide. Melting point 85°-86° C.

Workup

  1. temperaturethe mixture was heated (temperature 80°-85° C.)
  2. temperatureunder reflux
  3. customThe solid matter was removed from the reaction mixture by filtration
  4. concentrationthe filtrate was concentrated
  5. washElution
  6. customwith methanol-dichloromethane (1:9) and recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6cd64761b1054919ad1dbdded544128f
Source dataset
uspto-grants-1990_04
Patent number
US04920230

Reaction notes

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