Iodine → HCID 178526495, compound

HRID 1746683Notes

Reaction equation

HRID 1746683 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]I.[OH-].[K+].S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C>[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 807IodineHCID 14797Potassium HydroxideHCID 215015-NitroindazoleHCID 146045Sodium dithionate

Product 1

HCID 178526495HCID 178526495, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 5-nitro-1H-indazole (Aldrich, 5.0 g; 30.7 mmol) in DMF (60 ml) was treated with iodine (15.6 g; 61.4 mmol) and potassium hydroxide (6.45 g; 115 mmol) at 65° C. After stirring at 65° C. for 1 hour the mixture was poured into saturated sodium metabisulfate solution (200 ml) and the solid removed by filtration, washed with water and dried to give the title compound as a light brown solid (8.9 g, quant).

Workup

  1. customthe solid removed by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-40ebf6cdbc714420a457f7176c25f184
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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