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

HRID 1886180Notes

Reaction equation

HRID 1886180 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 1 1/2 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 p87, 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. 1H NMR (300 MHz, CDCl3) 2.58 (3H, s), 2.61 (3H, s), 7.22 (1H, s).

Workup

  1. temperatureat reflux for 1 1/2 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-59058ff6668242a088f5844b68ff040a
Source dataset
uspto-grants-1992_09
Patent number
US05149814

Reaction notes

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