Iodine → HCID 178468648, compound

HRID 1096998Notes

Reaction equation

HRID 1096998 reaction equation
[I:1]I.[OH-].[K+].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[CH:7]=[N:6]1.O.[Cl-].[NH4+]>CN(C=O)C>[I:1][C:7]1[C:8]2[C:13](=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)[NH:5][N:6]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 19737203Ethyl 1H-indazole-6-carboxylateHCID 57429219Ammonium chloride monohydrate

Product 1

HCID 178468648HCID 178468648, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 3.0-liter egg plant type flask, iodine (6.09 g, 24 mmol) and KOH (4.49 g, 68 mmol) were added to a DMF solution (60 mL) of ethyl 1H-indazole-6-carboxylate (4.52 g, 20 mmol), and stirred at room temperature for 2 hours. Saturated ammonium chloride water was added to it, extracted with ethyl acetate, washed with water and saturated saline water in that order, and dried with sodium sulfate. The reaction solution was filtered, concentrated, and the resulting solid was washed with a mixed solution of hexane and ethyl acetate to obtain the title compound as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated saline water in that order
  3. dry with materialdried with sodium sulfate
  4. filtrationThe reaction solution was filtered
  5. concentrationconcentrated
  6. washthe resulting solid was washed with a mixed solution of hexane and ethyl acetate

Sources & evidence

ORD record
ord-5348513a45e94c0dbbd84d72c5443c50
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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