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

HRID 892769Notes

Reaction equation

HRID 892769 reaction equation
[CH3:1][C:2]1[CH:7]([N+:8]([O-:10])=[O:9])[C:6](=O)[CH:5]=[C:4]([CH3:12])[N:3]=1.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 781987842,6-Dimethyl-3-nitro-4-pyridone

Product 1

HCID 107027254-Chloro-2,6-dimethyl-3-nitropyridine

Procedure

By the method of Yakugaku Zasshi, 87, 387 (1967), 2,6-dimethyl-3-nitro-4-pyridone (11.23 g, 66.8 mmol) and phosphorus oxychloride (57 ml) were heated together at reflux for 11/2 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 pH 7, and then the organic phase was separated, dried (MgSO4) and concentrated under reduced pressure to give a pale yellow solid, (9.8 g, 79%). Caution: this compound is believed to be a powerful skin irritant.

Workup

  1. temperatureat reflux for 11/2 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
  8. customto give a pale yellow solid, (9.8 g, 79%)

Sources & evidence

ORD record
ord-fa9575c72e164083b4cc7253f965c478
Source dataset
uspto-grants-1992_06
Patent number
US05120747

Reaction notes

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