Hydrochloric Acid → 5-Chloro-1-nitrosoindoline

Participants

Reaction Steps

A mixture of 77 g. (0.5 mole) of 5-chloroindoline, 80 ml. of concentrated hydrochloride acid and 500 ml. of crushed ice was stirred while a solution of 35 g. of sodium nitrite in 100 ml. of water was added over five minutes. The temperature was kept between 10°C. to 15°C. by addition of ice. The mixture was stirred for 1 hour and then filtered. Recrystallization of the product from benzene-isooctane gave 57 g. (68%) of product which melted at 120°-122°C.

Provenance & Evidence