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

HRID 1693345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693345
[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-4568232b2e7842e1a3ce532e7cb3cb96
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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