Iodine → HCID 178526460, compound

HRID 2110264Notes

Reaction equation

HRID 2110264 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[I:13]I.[OH-].[K+].OS([O-])=O.[Na+]>CN(C=O)C>[I:13][C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:10][N:9]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 242396-NitroindazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 178526460HCID 178526460, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Nitro-indazol (4.0 g, 24.52 mmol), prepared using the procedure of Tetrahedron (1999), 6917-6922, was dissolved in 60 mL of DMF and iodine (12.4 g) and KOH (5.23 g) were added successively. The reaction mixture was stirred at room temperature for 1.5 hours, then poured into 10% aqueous NaHSO3. The aqueous mixture was extracted three times with 150 mL EtOAc, and the combined organic layers were washed with water and brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give 7.01 g of crude 3-Iodo-6-nitro-1H-indazole.

Workup

  1. extractionThe aqueous mixture was extracted three times with 150 mL EtOAc
  2. washthe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a78d0a83731419a807bb3aef41f1b0d
Source dataset
uspto-grants-2009_04
Patent number
US07517901B2

Reaction notes

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