Journal of Organic Chemistry p. 513 - 517 (1986)
Update date:2022-08-17
Topics:
Lunn, George
Sansone, Eric B.
Nickel-aluminum alloy in dilute base can be used to reduce a variety of pyridines, quinolines, and isoquinoline to the corresponding piperidines, 1,2,3,4-tetrahydroquinolines, and 1,2,3,4-tetrahydroisoquinoline in good yield.The reaction is simple to perform, and high temperatures, high pressures, or hydrogen atmospheres are not required.The reaction is accelerated by substituents in the 2-position and by electron-withdrawing groups in the 3- and 4-positions while electron-supplying groups in the 3- and 4-positions retard the reaction.The major product isolated from the reduction of 2-phenylpyridine was 2-cyclohexylpiperidine hydrochloride.With isoniazid (1) and iproniazid (4) the pyridine ring is hydrogenated before the hydrazine is cleaved.
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