Silver complexes quinolinic acid

A quinoline—bromine adduct in hot carbon tetrachloride containing pyridine gives a 90% yield of 3-bromoquinoline (21) 3-chloroquinoline [612-59-9] is prepared by an analogous route, but in poorer yield. A quinoline—aluminum chloride complex heated with bromine gives a 78% yield of 5-bromoquinoline [165-18-3] (22). Equal quantities of 5- and 8-bromoquinoline [16567-18-3] are formed when quinoline is treated with one equivalent of bromine in concentrated sulfuric acid containing silver sulfate (23). 

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