Quinoline 4,6-dimethyl-, ring synthesis

The ring expansion of nitronaphthalenes with dimethyl phosphite and sodium methoxide in the presence of strong base to give 2-benzazepines (see Section 3.2.1.4.2.1.) has been adapted successfully to the synthesis of pyridoazepines, e.g. 24, 25, and 26, from 5-, 6-, and 8-nitro-quinoline, respectively43... 

Reduction of the heterocyclic ring and incorporation of a nitro function affords a compound with antischistosomal activity, oxamniquine (60). Its synthesis begins with chlorination of 2,6-dimethyl-quinoline, which proceeds regiospecifically on the methyl group adjacent to the ring nitrogen (56). 

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