Pyridine, 2-methyl-4-nitro-, 1-oxide → 2-Methyl-4-methoxypyridine-N-oxide

HRID 963476Notes

Reaction equation

HRID 963476 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([CH3:11])[N+:7]([O-:10])=[CH:8][CH:9]=1)([O-])=O.[CH3:12][O-:13].[Na+].[Na]>CO>[CH3:12][O:13][C:4]1[CH:5]=[C:6]([CH3:11])[N+:7]([O-:10])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxideHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 107018932-Methyl-4-methoxypyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 4-nitro-2-picoline-1-oxide (0.952 g) in dry methanol (20 ml) was added dropwise a solution of sodium methox-ide prepared from sodium (0.60 g) and methanol (10 ml) under stirring at cooling in an ice-bath. The mixture was stirred for 3 hours under the same condition. The resultant mixture was concentrated in vacuo. The residue was treated with chloroform and water. The organic layer was washed with water and a brine, and dried over sodium sulfate. Removal of the solvent gave 4-methoxy-2-picoline-1-oxide (0.958 g).

Workup

  1. temperatureat cooling in an ice-bath
  2. stirringThe mixture was stirred for 3 hours under the same condition
  3. concentrationThe resultant mixture was concentrated in vacuo
  4. additionThe residue was treated with chloroform and water
  5. washThe organic layer was washed with water
  6. dry with materiala brine, and dried over sodium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-01421a82ed62449a881d07663b2ff38e
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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