N-prop-2-ynylphthalimide → 3-Hydroxy-2-(prop-2-yn-1-yl)-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Steps

A mixture of 10 g of N-propargylphthalimide and 2 g of sodium borohydride in 100 ml of ethanol was heated on the steam bath for 15 minutes with stirring. The resulting solution was concentrated under reduced pressure to one third of the volume and the product was crystallized by addition of ice and saturated sodium bicarbonate solution. The precipitated crystals of the title compound were collected by filtration, washed with water and sucked dry. After drying in vacuum they had m.p. 157°-159° C.

Provenance & Evidence