Sodium Methoxide → 4-Methoxy-2,3,5-trimethylpyridine 1-oxide

HRID 1379086Notes

Reaction equation

HRID 1379086 reaction equation
[CH3:1][O-:2].[Na+].[N+]([C:7]1[C:12]([CH3:13])=[CH:11][N+:10]([O-:14])=[C:9]([CH3:15])[C:8]=1[CH3:16])([O-])=O>CO>[CH3:1][O:2][C:7]1[C:12]([CH3:13])=[CH:11][N+:10]([O-:14])=[C:9]([CH3:15])[C:8]=1[CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxide

Product 1

HCID 107022374-Methoxy-2,3,5-trimethylpyridine 1-oxideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide, prepared from Na (8.62 g, 0.375 mol) and MeOH (500 ml), was added 4-nitro-2,3,5-trimethylpyridine-N-oxide (45.5 g, 0.25 mol). The reaction mixture was refluxed for 5 h, cooled to rt and most of the solvent removed in vacuo. The slurry was diluted with water (100 ml) and extracted with CH2Cl2 (3×100 ml). The extracts were combined, washed with sat. NaCl solution, dried (MgSO4) and the solvent removed in vacuo to give 4-methoxy-2,3,5-trimethylpyridine-N-oxide as a semi-solid (37.5 g, 90%).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customremoved in vacuo
  3. additionThe slurry was diluted with water (100 ml)
  4. extractionextracted with CH2Cl2 (3×100 ml)
  5. washwashed with sat. NaCl solution
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-eb72b37c661a4ec3ac7911fc6f47e7f6
Source dataset
uspto-grants-1997_09
Patent number
US05670526

Reaction notes

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