Sodium Carbonate → 4-Chloro-7-methoxy-1,6-naphthyridine

HRID 40255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40255
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[CH:8]=[CH:9][NH:10]2)=[CH:5][N:4]=1.C(=O)([O-])[O-].[Na+].[Na+].O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)[N:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 534871227-Methoxy-1H-1,6-naphthyridin-4-one

Produkt 1

HCID 594273184-Chloro-7-methoxy-1,6-naphthyridine

Versuchsvorschrift

A two neck round bottomed flask equipped with CaCl2 guard tube was charged with 7-Methoxy-1H-[1,6]naphthyridin-4-one (28 g, 159 mmol) and POCl3 (280 mL). The reaction mixture was stirred at RT for 3 h. The reaction mixture was poured into ice water and the pH was carefully adjusted to 8 with solid sodium carbonate (highly exothermic reaction). The product was extracted with EtOAc. The combined organic layer was washed with water, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography on silica gel (230-400 mesh) eluting with ethyl acetate hexane mixture.

Aufarbeitung

  1. customA two neck round bottomed flask equipped with CaCl2 guard tube
  2. customhighly exothermic reaction)
  3. extractionThe product was extracted with EtOAc
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography on silica gel (230-400 mesh)
  8. washeluting with ethyl acetate hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-714069789492440bac160f7568ab3000
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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