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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence