The synthesis of substances allied to cotarnine / by Arthur H. Salway.

  • Salway, Arthur H. (Arthur Henry)
Date:
[1909?]
Catalogue details

Licence: In copyright

Credit: The synthesis of substances allied to cotarnine / by Arthur H. Salway. Source: Wellcome Collection.

    18/22 (page 1219)
    methyl alcohol, were heated for several hours with an excess of methyl iodide and sodium methoxide. The methyl alcohol was then removed, water added to the residue, and the mixture extracted with chloroform. The chloroform solution was washed, dried, and the solvent removed, when a solid residue was obtained which crystallised from alcohol in well-formed, colourless needles, melting at 179° : 0*0904 gave 0*2045 C02 and 0*0379 H20. 0 = 61*7; H = 4*7. C12Hn04N requires C = 6T8 ; H = 47 per cent. This compound possesses only feebly basic properties, and is insoluble in cold dilute hydrochloric acid. Oxyi&ocotarnine (y2-Keto-^>{p)-methoxy-^ : 7-methylenedioxy-l-methyl- 1:2:3: 4-tetrahydroquinoline). ch2-cit NMe-CO OMe One gram of the compound just described was reduced in dilute alcoholic solution by means of 200 grams of sodium amalgam (3 per cent.). During the course of the reaction the mixture was constantly agitated, and from time to time small quantities of hydrochloric acid were added to prevent the accumulation of alkali in the solution. After a short time a small quantity of solid separated, which at the end of the reaction was collected. It was only sparingly soluble in hot alcohol, from which it crystallised in rhombohedral prisms, melting at 280°. This substance was apparently a polymerised reduction product, similar in character to the products of high molecular weight obtained on reducing ketomethoxymethylenedioxydihydroquinoline. The filtrate from which the above compound had been separated was acidified with dilute hydrochloric acid, distilled in a current of steam to remove the alcohol, then rendered alkaline, and extracted with ether. This removed a viscid oil, which rapidly solidified, and when crystallised from dilute alcohol, separated in flat plates, melting at 113° : 0-0881 gave 0-1982 C02 and 0-0447 H,0. C = 61*4; H = 56. C12ff)304N requires 0 = 61-3; H = 55 per cent. It is evident from these results that the reduction of 2-keto- 8(5)-methoxy-6 : 7-methylenedioxy-l-methyl-1 : 2-dihydroquinoline by means of sodium amalgam effects the addition of two atoms of hydrogen only. The product, therefore, is isomeric with oxy- cotarnine. 0xyisocotcirnine possesses only feebly basic properties, since its hydrochloride dissociates in the presence of water. It is readily