The electrolytic reduction of phthalimides. I was written by Sakurai, Buhei. And the article was included in Bulletin of the Chemical Society of Japan in 1930.Electric Literature of C14H11NO This article mentions the following:
An alc. HCl solution of phthalimide (I) was electrolyzed between Pb electrodes, at 20 amp./sq. dm. and at 20-30°, yielding hydroxyphthalimidinc, m. 105°, needles. Reisert’s hydroxyphalimidine, m. 171° (cf. C. A. 7,2578), was found to be a polymer containing 2 mols. It was also prepd from alc. H2SO4 solution Cu electrodes, being used. With stronger acid, at 60 amp./sq. dm. and at 30-40°, Phthalimidine, m. 149°, needles, was obtained. Phthalimide could not be reduced in 2 N NaOH, but hydrolyzed to phthalamic acid and phthalic acid. Methylphthalimide (II) yielded methylphthalimidine, m. 45°, plates, with Pb cathode; with Cu cathode it yielded methylhydroxyphthalimidine, m. 129°, prisms. In alk. solution II hydrolyzed to phthalic acid and MeNH2. Ethylphthalimide (III) yielded ethylphthalimidine, colorless oil, with Pb electrodes; with Cu or Ni cathode ethylhydroxyphthalimidine was obtained instead. In alk. solution III hydrolyzed to ethylphthalamic acid, m. 136°, needles, also phthalic acid and EtNH2. Phenylphthalimide (IV) yielded phenylphthalimidine, scaly crystals. Hydroxyphenylphthalimide could not be obtained. In alk. solution IV hydrolyzed completely into phthalic acid and PhNH2. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).
2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C14H11NO
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles