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

HRID 35465

Reaction equation

HRID 35465 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].[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][C:6]1[CH:5]=[CH:4][N+:3]([O-:12])=[C:2]([CH3:1])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 1482232,3-Dimethyl-4-nitropyridine-N-oxideHCID 10942334Sodium Methoxide

Product 1

HCID 10630707Pyridine, 4-methoxy-2,3-dimethyl-, 1-oxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.5 g (0.015 mol) of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of abs. methanol is treated with 0.883 g of sodium methylate, whereupon the mixture is stirred at room temperature under argon for 2 days. The reaction mixture is concentrated and the residue is extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase is dried and evaporated. The residue, crystallized from methylene chloride/ ether, gives 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80°-83°.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionthe residue is extracted with methylene chloride and saturated sodium chloride solution
  3. dry with materialThe methylene chloride phase is dried
  4. customevaporated
  5. customThe residue, crystallized from methylene chloride/ ether

Sources & evidence

ORD record
ord-3bf28547df6047c298170f041a6da9a4
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Linked notes

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