Phosphorus oxychloride → 4-Chloro-2,6-dimethyl-3-nitropyridine

HRID 1088666Notes

Reaction equation

HRID 1088666 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:12])=[CH:5][C:6](=O)[C:7]=1[N+:8]([O-:10])=[O:9].P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:6]1[CH:5]=[C:4]([CH3:12])[N:3]=[C:2]([CH3:1])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 5492052,6-Dimethyl-3-nitropyridin-4(1H)-one

Product 1

HCID 107027254-Chloro-2,6-dimethyl-3-nitropyridineYield 79%

Procedure

By the method of Yakugaku Zasshi, 87, 387 (1967), 2,6-dimethyl-3-nitro-4(1H)-pyridone (see part (a)) (11.23 g, 66.8 mmol) and phosphorus oxychloride (57 ml) were heated together at reflux for 1.5 hours. The excess reagent was removed under reduced pressure, and the residue dissolved in dichloromethane (150 ml). This solution was treated with dilute aqueous sodium bicarbonate until the aqueous layer was at pH7, then the organic phase was separated, dried (MgSO4) and concentrated under reduced pressure to give the title compound as a pale yellow solid, (9.8 g, 79%). Caution: this compound is a potential skin irritant.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe excess reagent was removed under reduced pressure
  3. dissolutionthe residue dissolved in dichloromethane (150 ml)
  4. additionThis solution was treated with dilute aqueous sodium bicarbonate until the aqueous layer
  5. customthe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-850c28e95b5045489a4cde5d4fe04488
Source dataset
uspto-grants-1990_10
Patent number
US04963560

Reaction notes

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