Methanol → 2-Methyl-4-methoxypyridine-N-oxide

HRID 638584Notes

Reaction equation

HRID 638584 reaction equation
[Na].[N+]([C:5]1[CH:6]=[C:7]([CH3:12])[N+:8]([O-:11])=[CH:9][CH:10]=1)([O-])=O.[CH3:13][OH:14]>>[CH3:12][C:7]1[CH:6]=[C:5]([O:14][CH3:13])[CH:10]=[CH:9][N+:8]=1[O-:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxideHCID 5360545Sodium

Product 1

HCID 107018932-Methyl-4-methoxypyridine-N-oxideYield 92%

Procedure

To a solution of sodium (4.6 g, 0.2 mole) in anhydrous methanol (140 ml) at 25° C. was added 4-nitro-2-picoline-N-oxide (31 g, 0.2 mole). The mixture was stirred for 11/2 hours and then filtered. The filtrate was evaporated and the residue extracted with ethyl acetate. The solution was filtered, evaporated and the oily residue distilled to give the title compound (25.7 g, 92%) b.p. 150° C. at 0.2 mm mercury.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. extractionthe residue extracted with ethyl acetate
  4. filtrationThe solution was filtered
  5. customevaporated
  6. distillationthe oily residue distilled

Sources & evidence

ORD record
ord-fd678afde7a347d4a47273f46d75a677
Source dataset
uspto-grants-1985_12
Patent number
US04562197

Reaction notes

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