Water → HCID 178526495, compound

HRID 1983482Notes

Reaction equation

HRID 1983482 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].[I:13]N1C(=O)CCC1=O.O.C(OCC)C>CN(C)C=O>[I: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

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 215015-NitroindazoleHCID 120273N-Iodosuccinimide

Product 1

HCID 178526495HCID 178526495, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 17.0 g of 5-nitroindazole in 100 ml dimethylformamide was added 24.6 g of N-iodosuccinimide at room temperature, and the mixture was stirred at 80° C. for 7 hours. After standing to cool, to the reaction mixture were added 150 ml of water and 200 ml of diethyl ether, and the resulting crystals were collected by filtration. The crystals were sequentially washed with water, isopropanol and diethyl ether, to give 27.5 g of the title compound as colorless crystals.

Workup

  1. temperatureto cool, to the reaction mixture
  2. filtrationthe resulting crystals were collected by filtration
  3. washThe crystals were sequentially washed with water, isopropanol and diethyl ether

Sources & evidence

ORD record
ord-9b76c6c384d74bd1a6e1050bc6473008
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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