7-Methyl-8-oxononanoic acid → 6-(4,5,6-triiodo-2,3-dimethyl-3H-3-indolyl)hexanoic acid

HRID 579404Notes

Reaction equation

HRID 579404 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]([C:22](=O)[CH3:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]>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]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])([CH3:12])[C:22]([CH3:23])=[N:10]2

Participants

4

Reactant 2

HCID 222668237-Methyl-8-oxononanoic acidHCID 866953333,4,5-Triiodophenylhydrazine

Product 1

HCID 717361666-(4,5,6-triiodo-2,3-dimethyl-3H-3-indolyl)hexanoic acidYield 23.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,4,5-triiodophenylhydrazine 2 g (4 mmol) and 1 g (5 mmol) of 7-methyl-8-oxononanoic acid was refluxed in 15 mL of acetic acid for 16 hours. The acetic acid was evaporated, and the residue was dissolved in CHCl3, and washed by aqueous NaHCO3 and water. The organic layer was dried with CaCl2 and solvent was removed under reduced pressure by a rotary evaporator. The residue was column purified (Silica gel 60, 0-4% methanol-chloroform) to give 0.6 g of 6-(4,5,6-triiodo-2,3-dimethyl-3H-3-indolyl)hexanoic acid. 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 8.02 (1H, s, arom.), 2.16 (3H, s, 2-CH3), 2.07 (2H, t, CH2COOH), 1.65-1.05 (6H, m, CH2), 1.26 (3H, s, CH3), 0.58-0.20 (2H, m, CH2).

Workup

  1. customThe acetic acid was evaporated
  2. dissolutionthe residue was dissolved in CHCl3
  3. washwashed by aqueous NaHCO3 and water
  4. dry with materialThe organic layer was dried with CaCl2 and solvent
  5. customwas removed under reduced pressure by a rotary evaporator
  6. custompurified (Silica gel 60, 0-4% methanol-chloroform)

Sources & evidence

ORD record
ord-8fae604a61664178813d40c37922aea8
Source dataset
uspto-grants-2015_05
Patent number
US09040721B2

Reaction notes

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