Hydrochloric Acid → 7-Methylisatin

Participants

Reaction Steps

Utilizing the general procedure, 3.30 g of 7-methyl-3-methylthiooxindole and an E.Q. of sublimed potassium t-butoxide in 250 ml of tetrahydrofuran was stirred and vigorously aerated for 6 h at 0° C. and 18 h at 25° C. Acidification with 1.42 ml of conc. hydrochloric acid in 20 ml of water, followed by addition of a saturated brine solution, gave an organic layer which was separated and worked up as described above to give 1.98 g of crude product. Recrystallization from methanol gave 1.09 g (40% yield) of 7-methylisatin, mp 268°-270° C.

Provenance & Evidence