Phosphorus pentachloride → 3-Chloropyridine-2-carbonitrile

HRID 233481

Reaktionsgleichung

Reaktionsgleichung von HRID 233481
O[C:2]1[C:3]([C:8]([NH2:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12]>P(Cl)(Cl)(Cl)=O>[Cl:12][C:2]1[C:3]([C:8]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 24819Phosphorus pentachlorideHCID 702773-Hydroxypicolinamide

Produkt 1

HCID 8182583-Chloropyridine-2-carbonitrileAusbeute 14,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxypicolinamide (2.00 g, 14.5 mmol) in phosphorus oxychloride (10 mL) at room temperature was added phosphorus pentachloride (6.00 g, 28.8 mmol). The mixture was heated at reflux for 90 min, and the solvent was removed by distillation. The residue was poured into water, the aqueous solution was neutralized by addition of sodium bicarbonate, and was extracted with ethyl acetate. The organic phase was filtered through silica gel, the filtrate was concentrated, and the residue was subjected to flash chromatography on silica gel, affording 300 mg of 3-chloro-2-cyanopyridine. 1H NMR (CDCl3) δ7.50 (dd, 1, J=4.8, 8.4), 7.89 (dd, 1, J=l.6, 8.4), 8.63 (dd, 1, J=l.6, 4.8).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 min
  3. customthe solvent was removed by distillation
  4. additionThe residue was poured into water
  5. additionthe aqueous solution was neutralized by addition of sodium bicarbonate
  6. extractionwas extracted with ethyl acetate
  7. filtrationThe organic phase was filtered through silica gel
  8. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1ee32c16c4734b3d888049e400d7701b
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05593986

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