Sodium Carbonate → 5-Chloro-2-methylpyridazin-3(2H)-one

HRID 2194416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194416
CO[C:3]1[CH:8]=[N:7][N:6]([CH3:9])[C:5](=[O:10])[CH:4]=1.P(Cl)(Cl)([Cl:13])=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O>[Cl:13][C:3]1[CH:8]=[N:7][N:6]([CH3:9])[C:5](=[O:10])[CH:4]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 107492595-Methoxy-2-methyl-3(2H)-pyridazinone

Produkt 1

HCID 129101445-Chloro-2-methylpyridazin-3(2H)-oneAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21908982Water methylene chlorideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 1.50 g (10.70 mmol) of 5-methoxy-2-methyl-2H-pyridazin-3-one and 7.8 ml (13.1 g, 85.6 mmol) of phosphorus oxychloride was heated at 110° C. for 2 h. After allowing to cool to room temperature, the mixture was poured into 100 ml of ice/water with vigourous stirring. After neutralization by addition of saturated sodium carbonate solution, the compound was worked up with methylene chloride/water, dried over magnesium sulfate and concentrated in vaccuo. The crude material was purified by flash chromatography on silicagel using a 80:20 mixture of ethyl acetate and heptane as eluant to yield 904 mg (6.25 mmol, 58%) of the title compound as a crystalline white solid, MS: 141.2 (M+H+).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vaccuo
  4. customThe crude material was purified by flash chromatography on silicagel
  5. additiona 80:20 mixture of ethyl acetate and heptane as eluant

Quellen und Nachweise

ORD-Eintrag
ord-cd77801c8af241e5aed21a8431e91a89
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334287B2

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