Hydrochloric Acid → 2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE

HRID 1633564Notes

Reaction equation

HRID 1633564 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CN(C)C1C=CC=CC=1.Br[CH:20]([CH3:31])[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=O.Cl>CC1C=CC=CC=1C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[C:20]2[CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 7732P-AnisidineHCID 2991022-bromo-1-(4-methoxyphenyl)propan-1-one

Product 1

HCID 108800612-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
170 °C

Procedure

0.38 mol of p-anisidine is added to 75 ml of N,N-dimethylaniline in a 1 liter reaction flask, heated to 170° C. while being stirred and then a solution of 0.18 mol of 2-bromo-4′-methoxypropiophenone in 240 ml of o-xylene is added in drops at this temperature. The strongly foaming mixture is refluxed for another 3 hours. After the solution is cooled, it is poured onto 600 ml of 2N HCl, stirred thoroughly and extracted three times with ethyl acetate. The organic extracts are washed twice each with 2N HCl and water, dried on magnesium sulfate (MgSO4) and liberated of solvent. For purification, the crude product is chromatographed on silica gel 60 with CH2Cl2 and then recrystallized from 96% ethanol.

Workup

  1. temperatureThe strongly foaming mixture is refluxed for another 3 hours
  2. temperatureAfter the solution is cooled
  3. stirringstirred thoroughly
  4. extractionextracted three times with ethyl acetate
  5. washThe organic extracts are washed twice each with 2N HCl and water
  6. customdried on magnesium sulfate (MgSO4)
  7. customFor purification
  8. customthe crude product is chromatographed on silica gel 60 with CH2Cl2
  9. customrecrystallized from 96% ethanol

Sources & evidence

ORD record
ord-39c69402f29a454086f377b771417097
Source dataset
uspto-grants-2003_01
Patent number
US06503938B1

Reaction notes

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