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

Reaction equation

[C:1]([C:9]1[CH:19]=[C:18](Cl)[CH:17]=[CH:16][C:10]=1[NH:11][C:12](=O)CI)(=O)C1C=CC=CC=1.[N-:21]=[N+]=[N-].[Na+].[OH-].[CH2:26]([N+](C)(C)C)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CO>[N:11]1[C:12]2[C:18](=[CH:19][CH:9]=[C:1]3[NH:21][C:32]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:26]3=2)[CH:17]=[CH:16][CH:10]=1

Participants

Procedure

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.