The conversion of isonicotinic acid and its derivatives to l-methylisonipecotic acid and its derivatives has been accomplished by several different series of reactions (1). In some instances incomplete reduction of the pyridine ring occurred giving dihydro-or tetrahydro-pyridines (la, b). Unfortunately, these partially reduced compounds were not completely characterized and the comparison of the various materials is difficult. We have had occasion to repeat certain of these procedures and as a result have found errors in the literature and are able to report additional derivatives of l-methylisonipecotic acid and 1-methyl-l,2,3,6-tetrahydroisonicotinie acid.Supniewski and Serafinowna (la) (referred to as SS in this paper) reported that the reduction of methyl isonicotinate methiodide (la) over Adams' catalyst gave either methyl 1-methylisonipecotate hydriodide (Ilia) or methyl 1-methyl-
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