Phosphorus oxychloride → 2-Chloro-3-methoxy-5-nitropyridine

Reaction equation

[CH3:1][O:2][C:3]1[C:4](=O)[NH:5][CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:14].P(Cl)(Cl)(Cl)=O>>[Cl:14][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([N+:9]([O-:11])=[O:10])=[CH:6][N:5]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 24819Phosphorus pentachloride

HCID 234561543-Methoxy-5-nitropyridin-2-ol

Product 1

HCID 234561522-Chloro-3-methoxy-5-nitropyridine

Procedure

3-Methoxy-5-nitro-2-pyridone (5.7 g, 0.034 mole) was added to a combination of phosphorus pentachloride (5.0 g) and phosphorus oxychloride (40 ml); the reaction mixture was refluxed for 2.5 hours, cooled, poured over ice/water (300 ml) and stirred for 30 minutes. The resulting solid was collected by filtration, washed with water and air dried; yield, 1.72 g (27 percent), m.p. 40° to 41° C.