N-Methylphthalimide

Chemical properties

White powder

The Uses of N-Methylphthalimide

Photoreduction of N-methylphthalimide (NMP) with 2,3-dimethyl-2-butene h and the selective electroreduction of N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one have been studied.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 497, 1979 DOI: 10.1021/jo01318a005

General Description

Photoreduction of N-methylphthalimide (NMP) with 2,3-dimethyl-2-butene has been studied. The selective electroreduction of N-methylphthalimide to 3-hydroxy-2-methyl-isoindolin-1-one in ionic liquids and phenol as a proton donor under silent and ultrasonic conditions has been reported. Single electron transfer (SET)-induced photochemical reaction of NMP with silyl enol ether has been investigated. Nitration of NMP is reported to afford “exclusively” 3-nitro-derivative.

Synthesis

N-methylphthalimide (NMP) was synthesized from phthalic anhydride (PA) and dimethyl carbonate (DMC) with N,N-dimethylformamide (DMF) as solvent and tetrabutylamonium bromide (TBBA) as phase transfer catalyst (PTC).

Purification Methods

Recrystallise the imide from absolute EtOH or AcOH (m 134o). The IR has max at 1780 and 1380cm -1. [Beilstein 21 H 461, 21 III/IV 5030.]