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

HRID 1886180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886180
[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]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 781987842,6-Dimethyl-3-nitro-4-pyridone

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-59058ff6668242a088f5844b68ff040a
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149814

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