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.

    16/22 (page 1217)
    Reduction of 2-Keto-$(5)-methoxy-6 : 7-methylenedioxy-l : 2-dihydro- quinoline. Two grams of the substance were dissolved in dilate alcohol and reduced by the action of 200 grams of sodium amalgam (31 per cent.) with constant stirring. After a short time a grey precipitate separated, and the liquid gradually acquired a red colour. When the reaction was complete, the grey precipitate was removed by filtration and washed with water. It was insoluble in acids or alkalis, and practically so in ethyl acetate, chloroform, alcohol, or ether, but could be crystallised from hot acetic acid, from which it separated in small, colourless needles. These did not melt when heated to 310°: 0-0905 gave 0-1994 C02 and 0-0400 H20. C = 60T ; H = 4*9. (OjjHjqO^)* requires C = 60*0; H = 4-5 per cent. It is evident from the properties of this compound that its formation is due to polymerisation and simultaneous reduction of the keto- methoxymethylenedioxydihydroquinoline. The alkaliee filtrate from which the above compound had been separated was heated on the water-bath to remove alcohol, and then acidified with dilute hydrochloric acid, when a colourless substance was precipitated. This was collected, washed, and crystallised from dilute acetic acid, from which it was deposited in colourless needles, melting at 290°. It was very sparingly soluble in water or alcohol, but more soluble in chloroform: 0*1051 gave 0*2307 C02 and 0-0439 H20. C = 59-9 ; H = 4-6. (CnH10O4N)* requires C = 60-0; 11 = 4-5 per cent. The analysis and the properties of this substance show that it possesses the same empirical formula as the previously isolated compound, and is likewise a polymerised reduction product of keto- methoxymethylenedioxydihydroquinoline. No other substance could be isolated from the products of this reaction. Ketomethoxymethylenedioxydihydroquinoline was next reduced by means of sodium amalgam in dilute acetic acid solution, but in this case, also, the chief products were the above-described polymerised compounds, melting at 290° and above 310° respectively. A small amount of substance melting at 120° was obtained, but not sufficient for its further examination.