3-Methyl-2-butanone → 4,5,6-triiodo-2,3,3-trimethyl-3H-indole

HRID 508293Notes

Reaction equation

HRID 508293 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:10]N)[CH:5]=[C:6]([I:9])[C:7]=1[I:8].[CH3:12][CH:13]([CH3:17])[C:14](=O)[CH3:15]>C(O)(=O)C>[I:1][C:2]1[C:7]([I:8])=[C:6]([I:9])[CH:5]=[C:4]2[C:3]=1[C:13]([CH3:17])([CH3:12])[C:14]([CH3:15])=[N:10]2

Participants

4

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 866953333,4,5-Triiodophenylhydrazine

Product 1

HCID 717360084,5,6-triiodo-2,3,3-trimethyl-3H-indoleYield 27.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2 g of 3,4,5-triiodophenylhydrazine, and 0.86 g (10 mmol) of 3-methyl-2-butanone were refluxed in 15 mL of acetic acid for 16 hours. The acetic acid was evaporated, the residue was dissolved in chloroform, washed with aqueous solutions of NaHCO3, followed by Na2S2O3 and water. The organic layer was dried and chloroform was removed under reduced pressure by a rotary evaporator. The residue was column purified (Silica gel 60, 0-2% methanol-chloroform) to give 0.6 g of 4,5,6-triiodo-2,3,3-trimethyl-3H-indole. 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 8.04 (1H, s, arom.), 2.19 (3H, s, 2-CH3), 1.30 (6H, s, C(CH3)2).

Workup

  1. customThe acetic acid was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with aqueous solutions of NaHCO3
  4. customThe organic layer was dried
  5. customchloroform was removed under reduced pressure by a rotary evaporator
  6. custompurified (Silica gel 60, 0-2% methanol-chloroform)

Sources & evidence

ORD record
ord-c8f6c027dbf84cdbb665f7d3bde2b94e
Source dataset
uspto-grants-2015_08
Patent number
US09095612B2

Reaction notes

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