Potassium Carbonate → 4-Chloro-5-methoxy-2-phenyl-3(2H)-pyridazinone

HRID 381864

Reaktionsgleichung

Reaktionsgleichung von HRID 381864
C1(N2C=C(Cl)C(Cl)[C:9](=[O:15])N2)C=CC=CC=1.[C:16]1([N:22]2[C:27](=[O:28])[C:26]([Cl:29])=[C:25](Cl)[CH:24]=[N:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:16]1([N:22]2[C:27](=[O:28])[C:26]([Cl:29])=[C:25]([O:15][CH3:9])[CH:24]=[N:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 728134,5-Dichloro-2-phenyl-3(2H)-pyridazinoneHCID 18991304HCID 18991304, Verbindung

Produkt 1

HCID 3498424-Chloro-5-methoxy-2-phenyl-3(2H)-pyridazinoneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The title compound was prepared according to the method of (S. Cho et al. described in J. Het. Chem., (1996), 33, 1579-1582), starting with the N-phenyl-dichloropyridazinone. A mixture of 2-phenyl-4,5-dichloro-3(2H)-pyridazinone (1 g, 4.1 mmol) and finely powdered, anhydrous K2CO3 (580 mg, 4.2 mmol) in 50 mL of methanol was heated at reflux for 5 hours and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The acetate layer was washed with water, and brine to provide 2-phenyl-4-chloro-5-methoxy-3(2H)-pyridazinone (yield: 920 mg, 95%). 1H NMR (300 MHz, DMSO-d6) δ 4.15 (s, 3H), 7.50 (m, 5H), 8.43 (s, 1H). MS (DCI/NH3) m/z 237 (M+H)+, 254 (M+NH4)+.

Aufarbeitung

  1. customThe title compound was prepared
  2. temperatureat reflux for 5 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between water and ethyl acetate
  5. washThe acetate layer was washed with water, and brine

Quellen und Nachweise

ORD-Eintrag
ord-926ab51aac9f4bd69fa2bfa9d76580d3
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307047B1

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