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

HRID 403604Notes

Reaction equation

HRID 403604 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-5f52743799ff4853b0b88731e520f277
Source dataset
uspto-grants-2014_06
Patent number
US08748446B2

Reaction notes

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