Hydrochloric Acid → 3-(3-Methoxyphenyl)indole

HRID 1489147Notes

Reaction equation

HRID 1489147 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH:6]=[CH:7]OC.[C:13]1([NH:19]N)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.[Cl-].[Na+]>C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:19][CH:7]=2)[CH:10]=[CH:11][CH:12]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7516PhenylhydrazineHCID 57248581Methyl (3-methoxystyryl) ether

Product 1

HCID 154287153-(3-Methoxyphenyl)indole

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 90 g portion of the abovementioned methyl (3-methoxystyryl) ether was dissolved in 100 ml of ethanol. Then the solution was added dropwise to a mixed solution of 59.3 g phenylhydrazine, 800 ml ethanol and 53 ml concentrated hydrochloric acid under reflux, and after the addition, reflux heating was continued for 2 more hours. The reaction mixture was then cooled to room temperature, and after adding water, sodium chloride and a small amount of ethyl acetate, the mixture was stirred and the precipitated crystals were collected by filtration. The crystals were dissolved in chloroform and washed with dilute hydrochloric acid and sodium bicarbonate aqueous solution. And the solution was dried and concentrated to obtain a residue. Then toluene was added to the residue, and after refluxed for one hour. After cooling, precipitated crystals were then collected by filtration to obtain 89.6 g of 3-(3-methoxyphenyl)indole.

Workup

  1. temperatureunder reflux
  2. additionafter the addition
  3. temperaturereflux
  4. temperatureheating
  5. filtrationthe precipitated crystals were collected by filtration
  6. dissolutionThe crystals were dissolved in chloroform
  7. washwashed with dilute hydrochloric acid and sodium bicarbonate aqueous solution
  8. customAnd the solution was dried
  9. concentrationconcentrated
  10. customto obtain a residue
  11. temperatureafter refluxed for one hour
  12. temperatureAfter cooling
  13. customprecipitated crystals
  14. filtrationwere then collected by filtration

Sources & evidence

ORD record
ord-a6500f2254a34099b8a941f7cb5e974f
Source dataset
uspto-grants-1997_10
Patent number
US05677326

Reaction notes

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