Acetic Acid → 2-(4-Methoxy-3,5-dimethylphenyl)-3-methylindole

HRID 2309403Notes

Reaction equation

HRID 2309403 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH2:9][CH3:10])[CH:5]=[C:4]([CH3:12])[C:3]=1[O:13][CH3:14].[C:15]1([NH:21]N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.Cl>C(O)C.O>[CH3:14][O:13][C:3]1[C:4]([CH3:12])=[CH:5][C:6]([C:8]2[NH:21][C:15]3[C:20]([C:9]=2[CH3:10])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 129634181-(4-Methoxy-3,5-dimethylphenyl)propan-1-one

Product 1

HCID 136701412-(4-Methoxy-3,5-dimethylphenyl)-3-methylindoleYield 62.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

5.0 g of 2,6-dimethyl-4-propionylanisole and 2.8 g of phenylhydrazine were dissolved in 30 ml of ethanol. A small amount of acetic acid was added under reflux for 30 minutes. After cooling, 10 ml of a 20% ethanol solution of hydrogen chloride was added to the reaction mixture, and the mixture was refluxed for 1.5 hours. The reaction mixture was cooled, poured into water, extracted with benzene, washed with water, and dried. The solvent was evaporated, and the residue was crystallized from benzene-hexane to give 4.3 g of 2-(4-methoxy-3,5-dimethylphenyl)-3-methylindole.

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureAfter cooling
  3. temperaturethe mixture was refluxed for 1.5 hours
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with benzene
  6. washwashed with water
  7. customdried
  8. customThe solvent was evaporated
  9. customthe residue was crystallized from benzene-hexane

Sources & evidence

ORD record
ord-5d813c2174c94bf3b27f28f1e5f7ede2
Source dataset
uspto-grants-1987_09
Patent number
US04695581

Reaction notes

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