Radical chain reductive dehalogenation of hetaryl halides promoted by methoxide ion was written by Zoltewicz, John A.;Oestreich, Terence M.;Sale, Alan A.. And the article was included in Journal of the American Chemical Society in 1975.Safety of 4-Methoxyisoquinoline This article mentions the following:
3-Iodopyridine and 4-bromoisoquinoline rapidly reacted with NaOMe at 165° to give mixture consisting of pyridine and isoquinoline, resp., as the major products along with the resp., substitution products 3-methoxypyridine and 4-methoxyisoquinoline. Reduction of 3-iodopyridine in NaOMe-Me3OD took place without the incorporation of a significant amount D at the 3 position of pyridine. Reduction of both the iodo and bromo compounds was inhibited by PhNO2, azoxybenzene, and 1,1-diphenylethylene, but not O, and was believed to take place by a radical chain process involving formation of 3-pyridyl and 4-isoquinolyl radical intermediates. Low concentrations of CuCl2 accelerated the methoxydehalogenation of both hetaryl halides so that substitution became the major reaction. In the presence of the radical initiator azobisisobutyronitrile (I) and NaOMe, the 2 halogenated reactants as well as 2- and 4-iodopyridines underwent rapid reductive dehalogenation at 100°. Kinetic studies carried out with the 3 isomeric iodopyridines showed that the rate of the reduction was limited by the decomposition of I and was independent of the identity of the iodide. In the presence of I-NaDMe-OeOd 3-iodopyridine largely free of D at position 3, indicating the formation of the 3-pyridyl radical intermediate. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Safety of 4-Methoxyisoquinoline).
4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Safety of 4-Methoxyisoquinoline
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem