5-chloro-2-methyl-3-phenyl-1H-indole

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3 g. of 2-methyl-3-phenyl-5-chloro-indole in a solvent mixture 7 ml. of toluene and 5 ml. of dimethylformamide is added to a suspension of 0.6 g. of 50% sodium hydride (in paraffin) in 5 ml. of toluene at 20° C. After the reaction mixture is stirred at 20° C. for one hour, a solution of 1.1 g. of chloroacetamide in 20 ml. of dimethylformamide is added thereto at 20° C., and the reaction mixture is stirred under reflux for 5 hours. The resultant mixture is diluted with water and is extracted with benzene. The organic layer is washed with water and dried over sodium sulfate. The solvent is removed to a residue, which is recrystallized from ethanol to give 1-carbamoylmethyl-2-methyl-3-phenyl-5-chloroindole, m.p. 223°-224° C. at 20° C at 20° C., and the reaction mixture is stirred under reflux for 5 hours is extracted with benzene The organic layer is washed with water dried over sodium sulfate The solvent is removed to a residue, which is recrystallized from ethanol