The orientation of the nitro-group in nitromyristicinic acid / by Arthur H. Salway.

  • Salway, Arthur H. (Arthur Henry)
Date:
[1911?]
Catalogue details

Licence: In copyright

Credit: The orientation of the nitro-group in nitromyristicinic acid / by Arthur H. Salway. Source: Wellcome Collection.

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    The present investigation was therefore undertaken with the object of ascertaining which of these formulae must be assigned to the nitromyristicinic acid prepared in the above-mentioned reaction. The method employed consisted in the conversion of the nitro- group of nitromyristicinic acid into a carboxylic group, when the product would be cotarnic acid (VI) or an isomeride, according as the constitution of nitromyristicinic acid is represented by formula I or II. This transformation was successfully accomplished accord¬ ing to the series of reactions represented below, and the final product was identified as cotarnic acid. Nitromyristicinic acid must therefore possess the constitution I, and is 6-nitro-5-methoxy- 3 : 4-methylenedioxybenzoic acid: CH3< cq9h no; CEL< OMe (I.) > CH2< CO,Et CN OMe (V.) C02Et N0o CH2< 0 OMe (III.) —>- ]C09Et NH„ OMe (IV.) 0 ^H2<Cq co2n co2h OMe (VI.) The determination of the position of the nitro-group in nitro¬ myristicinic acid establishes, in addition, the constitutions of nitro- myristicinaldehyde (loc. cit., p. 1160), and of a series of synthetic products derived from the latter compound * (Trans., 1909, 95, 1204). Experimental. For the purpose of this investigation it was necessary to prepare a considerable quantity of nitromyristicinic acid. The method already described for the preparation of this compound (Trans., 1909, 95, 1165) is unsatisfactory, since approximately 60 per cent, of the myristicinic acid is converted into 5-nitro-l-methoxy- 2: 3-methylenedioxybenzene by elimination of carbon dioxide. It has now been found, however, that by esterification of the myristicinic acid prior to nitration the secondary change is entirely avoided. * These compounds comprise : o>‘2*dinitro-3-methoxy-4 : 5-methylenedioxy * styrene; 2-nitro-3-ruetlioxy-4 : 5-methylenedioxycinnamicacid ; 2-amino-3-methoxy- 4 : 5-methylenedioxycinnamic acid ; 2-keto-8-methoxy-6 : 7-methylenedioxy-l : 2-di- hydroquinoline ; 8-methoxy-6 : 7-methylenedioxycarbostyril methyl ether ; 2-keto-8- methoxy-1 -methyl-6 ; 7-methylenedioxy-l : 2-dihydroquinoline and oxywocotarnine.