Phenanthridine Chichibabin amination

Nucleophilic substitution of phenanthridine always takes place at the 6-position with organolithium compounds, as in the Chichibabin amination and Ziegler reaction. 

Phenanthridine is known to undergo direct amination readily with hydride extrusion (the Chichibabin reaction) and further examples have been reported.22 More interesting is the preparation of 6-aminophenanthridine in high yield by the action of the sodium salt of N,N-dimethylhydrazine on phenanthridine in benzene. The adduct (224) (R = Me) loses dimethylamine on heating leaving the sodium salt of the 6-amino compound (225).318... 

---