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

HRID 979848Notes

Reaction equation

HRID 979848 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-18e6086a0ce944ee9dc67a26a9bf246a
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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