1-Propanol → 2,3-Dimethyl-4-propoxypyridine 1-oxide
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
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
- concentrationThe reaction mixture is concentrated, whereupon the residue
- additionis treated with methylene chloride-water