Iodine → 3-Iodo-5-nitro-1H-indole

HRID 2357104Notes

Reaction equation

HRID 2357104 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>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

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 225235-Nitroindole

Product 1

HCID 231439973-Iodo-5-nitro-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

25.0 g (154.2 mmol) 5-nitroindole (Aldrich N1, 760-2) and 21.7 g (386.7 mmol) potassium hydroxide were dissolved in 270 ml DMF. To this solution 39.5 g (155.6 mmol) iodine dissolved in 250 ml DMF were added drop wise during one hour. The resulting mixture was subsequently stirred for 1.0 h at room temperature. Afterwards the reaction mixture was poured on 2.5 l of sludge. The formed precipitate was collected by filtration and washed twice with water. The residue obtained was dried in a vacuum (yield: 43.0 g).

Workup

  1. additionwere added drop wise during one hour
  2. additionAfterwards the reaction mixture was poured on 2.5 l of sludge
  3. filtrationThe formed precipitate was collected by filtration
  4. washwashed twice with water
  5. customThe residue obtained
  6. customwas dried in a vacuum (yield: 43.0 g)

Sources & evidence

ORD record
ord-1544b1232e394fdeba0840901ba40c22
Source dataset
uspto-grants-2010_07
Patent number
US07759470B2

Reaction notes

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