Water → 5-hydroxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 333727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333727
[I-].[Na+].Cl[Si](C)(C)C.C[O:9][C:10]1[C:11](=[O:28])[C:12]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[CH:19][CH:18]=2)=[N:13][N:14]([CH3:16])[CH:15]=1.O>C(#N)C>[OH:9][C:10]1[C:11](=[O:28])[C:12]([C:17]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[CH:19][CH:18]=2)=[N:13][N:14]([CH3:16])[CH:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 895866615-methoxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Produkt 1

HCID 895867365-hydroxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-oneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of sodium iodide (3.75 g) in acetonitrile (150 mL) was added chlorotrimethylsilane (3.17 mL) with stirring at room temperature, and the mixture was stirred for min. Then, 5-methoxy-1-methyl-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (1.41 g) was added, and the mixture was stirred for 30 min at the same temperature, and further refluxed for 3 hr. The reaction mixture was allowed to cool to room temperature, poured into water and the mixture was stirred for 30 min. The mixture was extracted with ethyl acetate, and the organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was triturated with ethyl acetate-diisopropyl ether, collected by filtration, and dried to give the title compound (1.032 g) as white needles.

Aufarbeitung

  1. stirringthe mixture was stirred for min
  2. stirringthe mixture was stirred for 30 min at the same temperature
  3. temperaturefurther refluxed for 3 hr
  4. temperatureto cool to room temperature
  5. stirringthe mixture was stirred for 30 min
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was triturated with ethyl acetate-diisopropyl ether
  11. filtrationcollected by filtration
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5099d1f4156645abae488f18998c305b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883788B2

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