1-Propanol → 2-Methyl-4-propoxypyridine-1-oxide

HRID 4698

Reaction equation

HRID 4698 reaction equation
[Na].[CH3:2][C:3]1[CH:8]=[C:7]([N+]([O-])=O)[CH:6]=[CH:5][N+:4]=1[O-:12].[CH2:13]([OH:16])[CH2:14][CH3:15]>>[CH3:2][C:3]1[CH:8]=[C:7]([O:16][CH2:13][CH2:14][CH3:15])[CH:6]=[CH:5][N+:4]=1[O-:12]

Participants

4

Reactant 3

HCID 10311-Propanol2×HCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxideHCID 5360545Sodium

Product 1

HCID 140971132-Methyl-4-propoxypyridine-1-oxide

Procedure

To a solution of sodium n-propoxide solution prepared by dissolving sodium (1.7 g) in n-propanol (200 ml) was added to a hot solution of 2-methyl-4-nitropyridine-1-oxide (5.2 g) in n-propanol (210 ml). The mixture was stirred for ten minutes, then n-propanol was evaporated off. To the residue was added chloroform under ice-cooling, and insoluble materials were removed by means of celite filtration. From the resultant solution was removed chloroform by evaporation. The residue was subjected to a silica-gel column chromatography, followed by elution with 10% methanol-chloroform to yield 2-methyl-4-propoxypyridine-1-oxide (4.7 g) as an oily substance.

Workup

  1. customn-propanol was evaporated off
  2. additionTo the residue was added chloroform under ice-
  3. temperaturecooling
  4. custominsoluble materials were removed by means of celite filtration
  5. customFrom the resultant solution was removed chloroform
  6. customby evaporation
  7. washfollowed by elution with 10% methanol-chloroform

Sources & evidence

ORD record
ord-3d549740ce134666822d464aa2a445ae
Source dataset
uspto-grants-1988_02
Patent number
US04727150

Linked notes

Loading…