Iodine → 3-iodo-1H-indole-5-carboxylic acid

HRID 1529361Notes

Reaction equation

HRID 1529361 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[I:15]I.S(=O)(=O)(O)[O-].[Na+]>CN(C=O)C>[I:15][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]([OH:12])=[O:11])[CH:5]=2)[NH:1][CH:2]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 742801H-Indole-5-Carboxylic AcidHCID 516919Sodium Bisulfate

Product 1

HCID 509905183-iodo-1H-indole-5-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-Indole-5-carboxylic acid (5 g, 31.05 mmol) in DMF (50 mL) was added KOH (5 g, 93.15 mmol) and I2 (15.7 g, 62.11 mmol). The reaction mixture was stirred at RT for 2 h and added 10% aqueous sodium bisulfate solution (25 mL). The resulting precipitate was collected by filtration, washed with water and dried under vacuum to obtain the title compound (8.0 g, 91%) as a brown solid. MS (ESI, pos. ion) m/z: 285.9 (M−1).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-1c4543a0694a477eae0cbacbda17f1b8
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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