3-(3-fluorophenyl)-6-nitro-1H-indazole → 3-(3-Fluorophenyl)-1H-6-indazolamine

HRID 1983469Notes

Reaction equation

HRID 1983469 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1>CO.C(OCC)(=O)C.[OH-].[Pd+2].[OH-].[C]>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 222608953-(3-fluorophenyl)-6-nitro-1H-indazole

Product 1

HCID 222606883-(3-Fluorophenyl)-1H-6-indazolamineYield 53.6%

Reagents, catalysts & solvents 3

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 300 mg of 3-(3-fluorophenyl)-6-nitro-1H-indazole in 5 ml methanol and 2.5 ml ethyl acetate was added 60 mg of 20% palladium hydroxide-carbon (water content: 50%), and the mixture was subjected to hydrogenation at room temperature at normal pressure for 7.5 hours. After adding 2.5 ml of ethyl acetate to the reaction mixture, the catalyst was filtered off through Celite. The solvent was evaporated, and the crude product was suspended in ethyl acetate-diisopropyl ether, to give 142 mg of the title compound as white crystals.

Workup

  1. filtrationthe catalyst was filtered off through Celite
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e2bea368a6b94fa4bec68e335ec0eeca
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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