Phosphorus oxychloride → 4-Chloro-1,5-naphthyridine

HRID 513749

Reaktionsgleichung

Reaktionsgleichung von HRID 513749
O=P(Cl)(Cl)[Cl:3].[N+:6]1([O-])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1>>[Cl:3][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][N:11]=2)[N:6]=[CH:7][CH:8]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 3392321-Oxo-1lambda~5~-1,5-naphthyridine

Produkt 1

HCID 5962624-Chloro-1,5-naphthyridineAusbeute 36 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

POCl3 (8.5 ml) was added to [1,5]naphthyridine 1-oxide 483 (0.85 g, 5.81 mmol) at 0° C. and the mixture was heated at 100° C. for 6 h. After cooling, the mixture was concentrated in vacuo, neutralized with NaHCO3 solution and the aqueous phase was extracted with EtOAc (40 ml). The organic phase was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (88:12) as the eluent to give the title compound (0.35 g, 36%).

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. extractionthe aqueous phase was extracted with EtOAc (40 ml)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with n-hexane/EtOAc (88:12) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-730196c261684ff9ad5320d336ba5b35
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

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