Water → HCID 178526495, compound

HRID 503143Notes

Reaction equation

HRID 503143 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-0b5ba4a3e7ef45bebb108ab564aedae6
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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