Acetic Acid → 1-(3-hydroxy-1-methyl-1H-indol-2-yl)ethanone

Participants

Reaction Steps

A mixture of 17.0 g (0.0637 mole) 1-(3-hydroxy-1-methyl-1H-indol-2-yl)-2-(methylsulfonyl) ethanone, 21.0 g (0.32 mole) zinc dust, 40 ml glacial acetic acid and 80 ml ab. ethanol was stirred vigorously and heated at 45°-50° for 1 hour. After stirring an additional hour at room temperature, the mixture was filtered through diatomaceous earth and the filter cake washed several times with fresh ethanol. The combined filtrates were condensed to 150 ml and 50 ml of hot water was added. Cooling yielded a green solid which was filtered, washed with cold water and recrystallized from 70% aqueous methanol to yield green needles of mpt. 119°-121°.

Provenance & Evidence