1,3-Diiminoisoindoline synthesis

Yield: 80%

Reaction Conditions:

with ammonia;sodium hydroxide in methanol at 20; for 3.75 h;Reflux;

Steps:

Method of the preparation of 1-imino-1H-isoindol-3-amine (1) with NaOH
Phthalonitrile (100 g, 0.78 mol) was mixed with methanol (500 mL). NaOH (0.92 g, 0.023 mol)was added, and ammonia was bubbled through the stirredsuspension for 45 min at room temperature. The mixture was brought to reflux and maintained at this temperaturefor 3 h while stirring and passing ammonia. Phthalonitrile dissolved and compound 1 precipitated. Upon cooling 50 gof bluish crystals of 1 were filtered off. The mother liquor was evaporated under reduced pressure to afford yellowish crude crystals. Methanol (200 mL) was added, and the mixture was heated to dissolve the crystals. After coolingand standing overnight, an additional amount of 1 (67 g, by1H NMR) was filtered off making a total yield of 80 %.

References:

Hordiyenko, Olga V.;Biitseva, Angelina V.;Kostina, Yuliya Yu.;Zubatyuk, Roman I.;Shishkin, Oleg V.;Groth, Ulrich M.;Kornilov, Mikhail Yu. [Structural Chemistry,2017,vol. 28,# 3,p. 607 - 616]