Chlorosuccinimide → HCID 20351108, compound

Participants

Reaction Steps

A solution of 7-methyl-3-methylthiooxindole (1 g, 0.0052 mol) and N-chlorosuccinimide (0.7 g, 0.0052 mol) in chloroform (100 ml) was stirred at room temperature for 1 hour. The solution was evaporated, yielding crude 3-chloro-7-methyl-3-methylthiooxindole, and the residue was dissolved in a minimum amount of tetrahydrofuran (ca. 10 ml) and added to a vigorously stirred slurry of red mercuric oxide (1.13 g, 0.0052 mol) and boron trifluoride ethereate (0,75, 0.0054 mol) in 50 ml of 20 percent aqueous tetrahydrofuran. After stirring at room temperature for 1 hour, 150 ml of ether was added, the reaction mixture was filtered through a pad of Celite, and the organic phase of the filtrate was separated, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated. The red residue was recrystallized from methanol to give 0.6 g (71%) 7-methylisatin, mp 267°-269°.

Provenance & Evidence