Addition of nitroalkanes toortho-halonitrobenzenes: A new synthesis of 4-chloro-7-(trifluoromethyl)quinoline

Article abstract of DOI:10.1016/S0040-4039(00)88734-1

Base-mediated reaction of ortho-nitroaryl chlorides and fluorides with nitroalkanes followed by an oxidative Nef reaction provides aryl ketones. With this simple procedure, methylketone 6 was prepared in 91% yield. 6 was then converted in three steps (60-65% yield) to 4-chloro-7-(trifluoromethyl)quinoline (2), an intermediate in the synthesis of the antihypertensive agent losulazine (U-54,669, 1).