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

HRID 2084283

Reaction equation

HRID 2084283 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalyst2×HCID 887MethanolSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b396a51757a74b9086b66f18d74683dc
Source dataset
uspto-grants-2004_04
Patent number
US06716856B1

Linked notes

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