Acetone → 7-Methoxy-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole

HRID 2084283

Reaktionsgleichung

Reaktionsgleichung von HRID 2084283
Br[CH:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[N:8]=[C:7]([CH3:17])[C:6]=2[C:5](=[O:18])[CH2:4][C:3]1([CH3:20])[CH3:19].C[C:22](C)=[O:23]>CO.[N+]([O-])([O-])=O.[Ag+]>[CH3:22][O:23][CH:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[N:8]=[C:7]([CH3:17])[C:6]=2[C:5](=[O:18])[CH2:4][C:3]1([CH3:20])[CH3:19]

Komponenten

5

Edukt 2

HCID 180AcetoneHCID 40739867-Bromo-3,6,6-trimethyl-1-pyridin-2-yl-5,7-dihydroindazol-4-one

Produkt 1

HCID 98606407-Methoxy-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazoleAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysator2×HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 0.1N silver nitrate in methanol (12 ml, 1.2 mmol) was added to a solution of 7-bromo-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole (0.2 g, 0.6 mmol), prepared as described in example 4, in acetone (12 ml). After stirring for about 48 hours, 6 ml of a 0.1N silver nitrate solution in methanol were added. The reaction mixture was stirred for further 72 hours and then filtered. The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane:ethyl acetate=90:10) to yield the title compound as a colourless solid (0.044 g, 25%): m.p. 86-89° C.

Aufarbeitung

  1. customprepared
  2. stirringThe reaction mixture was stirred for further 72 hours
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. customthe residue was chromatographed on silica gel (cyclohexane:ethyl acetate=90:10)

Quellen und Nachweise

ORD-Eintrag
ord-b396a51757a74b9086b66f18d74683dc
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716856B1

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