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

HRID 1680391Notes

Reaction equation

HRID 1680391 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

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 234561543-Methoxy-5-nitropyridin-2(1H)-one

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.

Workup

  1. temperaturethe reaction mixture was refluxed for 2.5 hours
  2. temperaturecooled
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water and air
  5. customdried
  6. customyield

Sources & evidence

ORD record
ord-1d39c78a682844d08c20700f1a49aed3
Source dataset
uspto-grants-1981_06
Patent number
US04273706

Reaction notes

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