Potassium Iodide → HCID 14279612, compound

HRID 1722469Notes

Reaction equation

HRID 1722469 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:16]=2[NH:15]C=[C:13]3[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:7])=[CH:4][CH:3]=1.[O:24]=[O+][O-].[I-].[K+].[C:29](OCC)(=O)[CH3:30]>C(O)C>[NH2:15][C:16]1[C:8]([C:6](=[O:7])[C:5]2[CH:22]=[CH:23][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:9][CH:10]=[CH:11][C:12]=1[C:13](=[O:24])[CH2:17][CH2:18][C:19]([O:21][CH2:29][CH3:30])=[O:20]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8857Ethyl AcetateHCID 24823Ozone2×HCID 14279610HCID 14279610, compound

Product 1

HCID 14279612HCID 14279612, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 13.1 g (0.04 mole) of 7-(4-chlorobenzoyl)-1H-indole-3-propanoic acid in 450 ml of ethyl acetate and 150 ml of absolute ethanol was treated with ozone until ozone was present above the solution. The solution was then stirred with an aqueous solution of potassium iodide, followed by a wash with aqueous sodium thiosulfate. The organic fraction was concentrated and the residue was dissolved in 250 ml of 190 proof ethanol. The solution was heated to reflux, 150 ml of 6N hydrochloric acid was added, and heating was continued for 18 hr. The mixture was diluted with 400 ml of water and a gummy solid separated. The gum was partitioned between dilute sodium hydroxide solution and methylene chloride. The basic aqueous fraction contained only a small amount of acidic material under acidification, so it was discarded. The methylene chloride layer was dried over anhydrous sodium sulfate and passed through a column of silica gel. The yellow-colored eluant was concentrated and the crystalline residue was recrystallized from cyclohexane to give 3.5 g (26%) of bright yellow powder, m.p. 112°-115° C.

Workup

  1. washa wash with aqueous sodium thiosulfate
  2. concentrationThe organic fraction was concentrated
  3. dissolutionthe residue was dissolved in 250 ml of 190 proof ethanol
  4. temperatureThe solution was heated
  5. temperatureto reflux
  6. addition150 ml of 6N hydrochloric acid was added
  7. temperatureheating
  8. additionThe mixture was diluted with 400 ml of water
  9. customa gummy solid separated
  10. customThe gum was partitioned between dilute sodium hydroxide solution and methylene chloride
  11. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  12. concentrationThe yellow-colored eluant was concentrated
  13. customthe crystalline residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-e797bf5536d74e3e8cb5cff9cabf319d
Source dataset
uspto-grants-1989_08
Patent number
US04855447

Reaction notes

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