Ammonium Chloride → 2-[2-(2-chlorophenyl)ethyl]-6-(4-fluoro-3-methylphenyl)-4-hydroxymethyl-2H-pyridazin-3-one

HRID 1348794

Reaktionsgleichung

Reaktionsgleichung von HRID 1348794
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([C:17](OC)=[O:18])=[CH:13][C:12]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([CH3:28])[CH:22]=2)=[N:11]1.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].[Cl-].[NH4+]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]([CH2:17][OH:18])=[CH:13][C:12]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([CH3:28])[CH:22]=2)=[N:11]1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 22347666cerium(III) chloride hexahydrateHCID 225622482-[2-(2-chlorophenyl)ethyl]-6-(4-fluoro-3-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one

Produkt 1

HCID 225623192-[2-(2-chlorophenyl)ethyl]-6-(4-fluoro-3-methylphenyl)-4-hydroxymethyl-2H-pyridazin-3-oneAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-[2-(2-chlorophenyl)ethyl]-6-(4-fluoro-3-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one (480 mg, 1.20 mmol) in THF/methanol (2 mL/1 mL), cerium(III) chloride hexahydrate (425 mg, 1.20 mmol) was added at −15° C., followed by the addition of sodium borohydride (45 mg, 1.20 mmol). After stirred for 10 minutes, a saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and was concentrated under reduced pressure. Further, the concentrate was purified by column chromatography on silica gel [hexane/ethyl acetate (2/1)] to yield the title compound as a pale yellow syrupy substance (yield: 11.0%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationwas concentrated under reduced pressure
  4. customFurther, the concentrate was purified by column chromatography on silica gel [hexane/ethyl acetate (2/1)]

Quellen und Nachweise

ORD-Eintrag
ord-c90e3851495f4d1a8a68fb66a7e26226
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211577B2

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