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

HRID 1610086Notes

Reaction equation

HRID 1610086 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-bd3e0ba39c434c3d9f7772da4b7e27fc
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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