Iodine → 1H-Indole-7-carboxaldehyde, 3-iodo-

HRID 1429595Notes

Reaction equation

HRID 1429595 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[O:11])[CH:3]=[CH:2]1.[I:12]I.[OH-].[K+]>CN(C)C=O>[I:12][C:3]1[C:4]2[C:9](=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 595414341H-Indole-7-carboxaldehyde, 3-iodo-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a starting material (indole-7-carbaldehyde), a solution of 24 g of I2 in 125 ml of DMF (dimethylformamide) was added with stirring, and 5.3 g of KOH was added, after which the mixture was allowed to react. The termination of the reaction was confirmed with thin layer chromatography (TLC), after which layer separation was conducted with 354 ml of EA and 354 ml of purified water. The organic layer was washed with aqueous 10% Na2S2O3, dried with Na2SO4 (sodium sulfate), filtered and concentrated at 40, thus obtaining P10 as a concentrated residue.

Workup

  1. customto react
  2. customafter which layer separation
  3. washThe organic layer was washed with aqueous 10% Na2S2O3
  4. dry with materialdried with Na2SO4 (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated at 40, thus obtaining P10 as a concentrated residue

Sources & evidence

ORD record
ord-7c85cfffad7d4df7bc8cd2d223882873
Source dataset
uspto-grants-2015_01
Patent number
US08940739B2

Reaction notes

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