Methyl iodide → 1H-Isoindole-1,3(2H)-dione, 2-methyl-4-nitro-

Participants

Reaction Steps

A solution of 3-nitrophthalimide (Aldrich)(1.78 g, 0.01 mol) in dry N,N-dimethylformamide (20 ml) was added dropwise to a stirred suspension of sodium hydride (0.36 g of an 80% dispersion in oil; 0.012 mol) in dry N,N-dimethylformamide (10 ml) under argon. The mixture was stirred at room temperature for 30 min and then treated with iodomethane (0.75 ml, 0.012 mol). After stirring overnight the reaction was poured into ice-water and extracted with dichloromethane (4×50 ml). The combined extracts were washed with water followed by brine, then dried over sodium sulfate and concentrated in vacuo. The residue was treated with water, and the resulting precipithate was removed by filtration and washed with water. After drying in a vacuum dessicator over silica gel the title compound was obtained as a yellow solid (1.64 g).

Provenance & Evidence