Acetic Anhydride → 1-(5-Bromo-3-methyl-1H-indazol-1-yl)ethan-1-one

HRID 38485

Reaktionsgleichung

Reaktionsgleichung von HRID 38485
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH2:16][CH3:17])[CH:10]=1.CC([O-])=O.[K+].[N:23](OCCC(C)C)=O.C1OCCOCCOCCOCCOCCOC1>C(Cl)(Cl)Cl>[C:5]([N:13]1[C:12]2[C:11](=[CH:10][C:9]([Br:8])=[CH:15][CH:14]=2)[C:16]([CH3:17])=[N:23]1)(=[O:7])[CH3:6]

Komponenten

7

Edukt 5

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 28012834-Bromo-2-ethylaniline

Produkt 1

HCID 591273821-(5-Bromo-3-methyl-1H-indazol-1-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

Acetic anhydride (4.73 ml) was added to the mixture of 4-bromo-2-ethylaniline (5.0 g) and KOAc (2.94 g) in CHCl3 (70 ml) and stirred for 30 minutes at reflux. Then isoamyl nitrite (6.65 ml) and 18-crown-6-ether (660 mg) was added to the reaction mixture and stirred for 12 h. under reflux. The reaction mixture was diluted with CHCl3, washed with water, and dried over sodium sulfate. After filtration and concentration, the residue was purified by silica gel chromatography (hexane/EtOAc), and crystallized from mixed solvent of hexane and CHCl3 to give intended compound as a yellow solid.

Aufarbeitung

  1. temperatureat reflux
  2. stirringstirred for 12 h.
  3. temperatureunder reflux
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by silica gel chromatography (hexane/EtOAc)
  8. customcrystallized
  9. additionfrom mixed solvent of hexane and CHCl3
  10. customto give

Quellen und Nachweise

ORD-Eintrag
ord-7b5dffd064424629bd0d34f8d159136b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524730B2

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