Water → 5-Chloro-n-aminoindoline

Participants

Reaction Steps

To a stirred mixture of 50 g. (0.27 mole) of 5-chloro-1-nitrosoindoline, 80 g. (1.2 mole) of zinc and 250 ml. of water was added over a 45 minute period 100 ml. of glacial acetic acid. The mixture was filtered, the filtrate basified with 50% sodium hydroxide solution and the base-insoluble oil extracted with ether. The combined ether extracts were dried, concentrated and the residual oil distilled. 1-Amino-5-chloroindoline was distilled at 96°-98°C./0.1 mm. The oil solidified on standing at room temperature.

Provenance & Evidence