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To prove that the Ziegler reaction proceeds in position 2 of 4-chloroquinoline, we synthesized 4-chloro-2-methylquinoline, 2, using methyllithium in 90% yield. The NMR spectrum was found to be identical to that of commercially available 2.
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We observed that the isolated 2-substituted 4-chloro-1,2-dihydroquinolines oxidize within a few days when exposed to air.
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POPd, POPd1, and POPd2 can be purchased from Combiphos Catalysts, Inc., New Jersey. Website: www.combiphos.com.
-
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71
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It should be noted that tri-n-butylethynylstannane and tri-n-butylvinylstannane did not undergo POPd-catalyzed Stille coupling with quinolines 2 and 5, respectively.
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72
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