1-Propanol → 2,3-Dimethyl-4-propoxypyridine 1-oxide

HRID 35455

Reaction equation

HRID 35455 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].[CH2:13]([OH:16])[CH2:14][CH3:15]>>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:16][CH2:13][CH2:14][CH3:15])[CH:5]=[CH:4][N+:3]=1[O-:12]

Participants

3

Reactant 2

HCID 10311-PropanolHCID 1482232,3-Dimethyl-4-nitropyridine-N-oxide

Product 1

HCID 150355372,3-Dimethyl-4-propoxypyridine 1-oxide

Procedure

25 g of 2,3-dimethyl-4-nitropyridine 1-oxide are dissolved in 1250 ml of n-propanol and the solution is stirred at 120° under argon for 16 days. The reaction mixture is concentrated, whereupon the residue is treated with methylene chloride-water and extracted. The organic phases are dried and concentrated. The residue is chromatographed on silica gel and purified with methylene chloride-methanol (20:1, 10:1), the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. The 2,3-dimethyl-4-propoxypyridine 1-oxide obtained is processed directly.

Workup

  1. concentrationThe reaction mixture is concentrated, whereupon the residue
  2. additionis treated with methylene chloride-water
  3. extractionextracted
  4. customThe organic phases are dried
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel
  7. custompurified with methylene chloride-methanol (20:1, 10:1)
  8. customthe pressure being produced with nitrogen gas

Sources & evidence

ORD record
ord-911e160eb839437f962e3aec63d48290
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Linked notes

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