Sodium Azide → 7H-Pyrido(3,2-c)carbazole

Participants

Reaction Steps

A solution of 120 g. of 2'-benzoyl-4'-chloro-2-iodo-acetanilide (mp 125°-127°) and 39.0 g. of sodium azide in 3.2 l of methanol was heated to reflux for 15 minutes. The mixture was allowed to cool at room temperature. A methanolic solution of benzyltrimethylammonium hydroxide (35% concentration, 25 ml.) was added while the mixture was still warm. After standing overnight, 70.5 g. (79%) of 3-azido-6-chloro-4-phenylcarbostyril, as yellow needles, were collected and washed with methanol, melting point was indefinite because of decomposition in the range of 120°-150°, forming high-melting indoloquinoline. An analytical sample was obtained by recrystallization from methanol.

Provenance & Evidence