Iodine → 3-Iodo-5-nitro-1H-indole

HRID 1529354Notes

Reaction equation

HRID 1529354 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[OH-].[K+].[I:15]I.S(=O)(=O)(O)[O-].[Na+]>CN(C=O)C>[I:15][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][CH:8]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 225235-NitroindoleHCID 516919Sodium Bisulfate

Product 1

HCID 231439973-Iodo-5-nitro-1H-indoleYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitro-1H-indole (5 g, 30.86 mmol) in DMF (50 mL) was added KOH (5 g, 92.58 mmol), followed by addition of I2 (15.7 g, 61.74 mmol). The reaction mixture was stirred at RT for 2 h and then added 10% aqueous sodium bisulfate (50 mL) solution. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to obtain the title compound as a pale yellow solid (8.0 g. 91%). MS (ESI, pos. ion) m/z: 286.9 (M−1)

Workup

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

Sources & evidence

ORD record
ord-ff0d112a858840b8b45af04f98f8b228
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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