Phosphorus oxychloride → 6-Chloro-2-methyl-3-nitropyridine

HRID 751601

Reaktionsgleichung

Reaktionsgleichung von HRID 751601
[CH3:1][C:2]1[NH:7][C:6](=O)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH3:1])[N:7]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 5430532-Hydroxy-6-methyl-5-nitropyridine

Produkt 1

HCID 2531236-Chloro-2-methyl-3-nitropyridine

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A suspension of 6-methyl-5-nitro-1H-pyridin-2-one (Preparation 2, 3.53 g, 22.9 mmol) in phosphorous oxychloride (20 mL) was heated to 115° C. (oil bath temperature) for 3 h then allowed to cool to rt. The phosphorous oxychloride was removed in vacuo and the residue poured into iced water (100 mL). The mixture was quenched by addition of saturated sodium bicarbonate solution, then the aqueous mixture was extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to furnish the title compound as a brown solid. δH (CDCl3): 2.86 (3H, s), 7.36 (1H, d, 8.59 Hz), 8.27 (1H, d, 8.32 Hz).

Aufarbeitung

  1. temperatureto cool to rt
  2. customThe phosphorous oxychloride was removed in vacuo
  3. additionthe residue poured into iced water (100 mL)
  4. customThe mixture was quenched by addition of saturated sodium bicarbonate solution
  5. extractionthe aqueous mixture was extracted with ethyl acetate (3×100 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f2140a0309264354811cbf5ca934c9c5
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405210B2

Verknüpfte Notizen

Wird geladen…