Methyl iodide → 4-[[2-[(n-butylmethylamino)methyl]-1H-indol-3-yl]methyl]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one

Participants

Reaction Steps

A solution of 2-n-Butyl-1,2,3,4-tetrahydropyrrolo[3,4-b]indole, 8.6 g., and methyl iodide, 2.6 ml. in dimethylformamide is stirred fifteen minutes, and then added all at once to a solution of the anion of the pyrazolone, prepared from 6.96 g. of 2-phenyl-5-methyl-3H-pyrazol-3-one and 2.0 g. fifty percent sodium hydride in dimethylformamide at 10°-20° C. The mixture is heated on a steam bath for one hour, then stirred at room temperature for sixteen hours. The reaction mixture is next poured into water, precipitating the product, 8.6 g., m.p. about 180°-200° with decomposition. Recrystallization from methanol gives 6.3 g., m.p. 195°-200° with decomposition.

Provenance & Evidence