5-Nitroindazole → HCID 178526490, compound

HRID 1983463Notes

Reaction equation

HRID 1983463 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:13][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1

Participants

5

Reactant 2

HCID 215015-NitroindazoleHCID 67184N-bromobutanimide

Product 1

HCID 178526490HCID 178526490, compoundYield 130.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 12.4 g of 5-nitro-1H-indazole in 100 ml carbon tetrachloride were added 16.2 g of N-bromosuccinimide and 0.62 g of 2,2′-azobisisobutyronitrile, and the mixture was heated under reflux for 1 hour. The reaction mixture was cooled, and the resulting crystals were filtrated and washed with diethyl ether, to give 24.0 g of the title compound as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe resulting crystals were filtrated
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-5bda01dd935f40c1968f6bfb6630f83f
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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