Phosphorus oxychloride → Ethyl 2-(4-(6-chloropyridazin-4-yl)phenyl)propanoate

HRID 407085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407085
O=[C:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=2)=[CH:3]1.P(Cl)(Cl)([Cl:23])=O>CN(C=O)C>[Cl:23][C:2]1[N:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=2)[CH:3]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 67980170Ethyl 2-(4-(6-oxo-1,6-dihydropyridazin-4-yl)phenyl)propanoate

Produkt 1

HCID 86667187Ethyl 2-(4-(6-chloropyridazin-4-yl)phenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of ethyl 2-[4-(6-oxo-1,6-dihydropyridazin-4-yl)phenyl]propanoate (0.48 g, 1.7 mmol) in phosphoryl chloride (5.0 mL) and DMF (50 μL) was stirred at 100° C. for 3 h. The solvent was removed and the residue was diluted with methylene chloride, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-20%) to afford the desired product. LCMS (M+H)+: m/z=299.1

Aufarbeitung

  1. customThe solvent was removed
  2. additionthe residue was diluted with methylene chloride
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-20%)

Quellen und Nachweise

ORD-Eintrag
ord-85e9d28aaf6f49f691406e1a09f4fb7f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754114B2

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