Phosphorus oxychloride → 2-Chloro-5-nitronicotinic acid

HRID 1078552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1078552
O[C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178524577HCID 178524577, Verbindung

Produkt 1

HCID 125426642-Chloro-5-nitronicotinic acid

Versuchsvorschrift

A solution of 2-hydroxy-5-nitronicotinic acid (9.2 g, 0.05 mol) in phosphorus oxychloride (25 ml) was refluxed for 5 hours. The solvent was removed in vacuo and the residue dissolved in a mixture of tetrahydrofuran and ether. After cooling the solution in an ice bath, water was cautiously added dropwise with stirring until a clean separation of layers was obtained. The organic layer was washed with water and a saturated sodium chloride solution, dried (anhydrous magnesium sulfate) and concentrated. Recrystallization from ether gave 6.94 g (69% of theory) of pure product, m.p. 135° C. (dec).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in a mixture of tetrahydrofuran and ether
  3. temperatureAfter cooling the solution in an ice bath
  4. additionwater was cautiously added dropwise
  5. customwas obtained
  6. washThe organic layer was washed with water
  7. dry with materiala saturated sodium chloride solution, dried (anhydrous magnesium sulfate)
  8. concentrationconcentrated
  9. customRecrystallization from ether
  10. customgave 6.94 g (69% of theory) of pure product, m.p. 135° C. (dec)

Quellen und Nachweise

ORD-Eintrag
ord-53f1f62e75934da2bd1d38e177bd1d76
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05550122

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