By R.H.F Manske, H.L. Holmes
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Extra info for Alkaloids: v. 3: Chemistry and Pharmacology
Subsequent investigation of this reaction by Rabe and Psaternack (208) revealed that phenyl-(Pquinolyl)-ketone is indeed formed, but that the melting point of this compound is 60”. In connection with their work on the synthesis of quininic acid and of cinchoninic acid, Kaufmann and his collaborators (178-180, 184) had prepared hyanc&-methoxyquinoline and 4-cyanoquinoline, obtained earlier by dehydration of cinchoninamide with thionyl chloride or with phosphorus pentoxide (209). Both products reacted with methylmagn d u m iodide in anisole solution and furnished methy1-(6-methoxy-P quinoly1)-ketone and methyl-(4quinolyl)-ketone respectively (210, 211).
It is now possible to write full structures (CXXXI, CXXXII, CXXXIII, CXXXIV) for each of the cinchona alkaloids. ~-6-0~ I 0 CXXIX T E E CHEMISTRY OF T E E CINCHONA ALKALOIDS 33 f& HO-- cxxxu quinidine cinchonhe & I Hd2 H2G\oH CXXXIII CXXXIV epiquinhe. 9 is of some interest.. The 0-toluenesulfonyl derivative of cinchonine is transformed by potassium benzoate into the benzoate of heterocinchonine (97-100). When the stereochemically similar quinidme 0-toluenemlfonate is treated with aqueous potash, it is converted in part into quinidine, and in larger measure to an unidentified oily product (164) ;analogy, and the considerations outlined below suggest that the latter material may be a mixture of htetoquinidine and anhydro bases.
Numerous other syntheses of this substance have since been recorded (199-203). An important contribution to the synthetic problem was made in 1921 by E. Koenigs and Ottmann (204),who extended previous work by Rabe and Kindler (205),on the preparation of 8-(4-piperidyl)-propionic acid (CLXVIII), to the synthesis of dl-homocincholoipon (CLXXII). 8-Collidine (CLXIX) was condensed with chloral, and an intermediate (CLXX) was obtained which yielded @-(3-ethylpyridyl)-4-acrylicacid (CLXXI) on alkaline hydrolysis.