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

HRID 703159Notes

Reaction equation

HRID 703159 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 of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of absolute methanol was treated with 0.883 g of sodium methylate, whereupon the mixture was stirred at room temperature under argon for 2 days. The reaction mixture was concentrated and the residue was extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase was dried and evaporated. The residue, crystallized from methylene chloride/ether, gave 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80-83°.

Workup

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

Sources & evidence

ORD record
ord-097d3333513e4127aa6abd0f833e4691
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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