Ethanol → HCID 14279611, compound

HRID 1722468Notes

Reaction equation

HRID 1722468 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16]C=[C:14]2[CH2:18][CH2:19][C:20]([OH:22])=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:25])C.O=[O+][O-].[I-].[K+]>C(OCC)(=O)C.C(O)(=O)C.O>[NH2:16][C:17]1[C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=[CH:12][C:13]=1[C:14](=[O:25])[CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

8

Reactant 4

HCID 702EthanolHCID 4875Potassium IodideHCID 24823OzoneHCID 14279609HCID 14279609, compound

Product 1

HCID 14279611HCID 14279611, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8.7 g (0.03 mole) of 7-benzoyl-1H-indole-3-propanoic acid in 300 ml of ethyl acetate and 100 ml of abs. ethanol was ozonized until ozone was present above the solution. The yellow solution was then treated with 16.6 g (0.1 mole) of potassium iodide in 30 ml of acetic acid and 30 ml of water. After stirring 1 hr, the liberated iodine was removed by washing with a 15% sodium thiosulfate solution and the yellow organic layer was concentrated. The residue was dissolved in 100 ml of ethanol and 20 ml of 6N hydrochloric acid and heated at reflux for 16 hr. The dark red solution was concentrated and the residue was partitioned between dil. sodium hydroxide and methylene chloride. The basic aqueous layer was made acidic and the pH was adjusted to 2-3 by the addition of dil. sodium hydroxide. The solid was collected and dried, then recrystallized from benzene isopropyl ether to give 5.9 g (67 %) of yellow powder, m.p. 161.0°-2.5° C.

Workup

  1. customthe liberated iodine was removed
  2. washby washing with a 15% sodium thiosulfate solution
  3. concentrationthe yellow organic layer was concentrated
  4. dissolutionThe residue was dissolved in 100 ml of ethanol
  5. temperature20 ml of 6N hydrochloric acid and heated
  6. temperatureat reflux for 16 hr
  7. concentrationThe dark red solution was concentrated
  8. customthe residue was partitioned between dil. sodium hydroxide and methylene chloride
  9. additionthe pH was adjusted to 2-3 by the addition of dil. sodium hydroxide
  10. customThe solid was collected
  11. customdried
  12. customrecrystallized from benzene isopropyl ether

Sources & evidence

ORD record
ord-8cde0e1bfb7f409b964cd18a1340e49e
Source dataset
uspto-grants-1989_08
Patent number
US04855447

Reaction notes

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