Synthesis of cotarnine / by Arthur H. Salway.

  • Salway, Arthur H. (Arthur Henry)
Date:
[1910?]
Catalogue details

Licence: In copyright

Credit: Synthesis of cotarnine / by Arthur H. Salway. Source: Wellcome Collection.

    6/16 (page 1211)
    The synthesis of cotarnine having now been accomplished, that of the alkaloid narcotine has become complete. The stages by which these syntheses have been effected may be represented by the following scheme: Myristicin Myristicinaldehyde 3-Methoxy-4 : 5-methylenedioxycinnamic acid #-3-Methoxy-4 : 5-methylenedioxyphenylpropionic acid $-3-Methoxy-4 : 5-methylenedioxyphenylpropionamide #-3-Methoxy-4 : 5-metliylenedioxyphenylethylamine Phenylacetyl-8-3-methoxy-4 : 5-methylenedioxyphenylethylamine 8-Methoxy-6 : 7-methylenedioxy-l-benzyl-3 : 4-dihydroMoquinoline 1-Benzylhydrocotarnine 4 Cotarnine Guaiacol Y Guaiacolcarb- oxylic acid Y 5:6-Dimethoxy- trichloro- methylphthal- ide Y 2-Carboxy-3 : 4- dimethoxy- mandelic acid Y Meconine t <7Z-Narcotine. Z-Narcotine. Experimental. B-3-M ethoxy-^: 5-methylenedioxyphenylpropionamide (V, p. 1209). For the preparation of this compound, 100 grams of j6-3-methoxy- 4 : 5-methylenedioxyphenylpropionic acid,* which had been obtained from myristicin by a series of reactions described in a previous investigation (Trans., 1909, 95, 1208—1210), were dissolved in benzene, and the solution gently warmed with 1 molecule of phos¬ phorus pentachloride until the reaction was complete. The mixture was then heated on the water-bath under diminished pressure for some time, whereby the solvent, and the phosphoryl chloride which had been formed, were completely removed. The residual crude acid chloride, dissolved in benzene, was gradually added, with vigorous agitation, to an excess of concentrated aqueous ammonia. The * The melting point of 8-3-methoxy-4 ; 5-methylenedioxyphenylpropionic acid was erroneously given as 124—125° in the previous paper (loc, cit.). The correct melting noint of this compound is 99—100°.