Researches on the constitution of physostigmine. Pt. III. The formation of substituted indoles from m-4-xylidine, and the reduction of 3-nitro-p-tolylacrylic acid / by Arthur H. Salway.

  • Salway, Arthur Henry.
Date:
1913
Catalogue details

Licence: In copyright

Credit: Researches on the constitution of physostigmine. Pt. III. The formation of substituted indoles from m-4-xylidine, and the reduction of 3-nitro-p-tolylacrylic acid / by Arthur H. Salway. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    stamce was collected and purified by crystallisation from chloro- form, when it was found to sinter at 160° and to become com- pletely melted at 164°: 0-0965 gave 0'2299 C02 and 0'0614 H20. C = 65’0; H = 7T. 0’10G3 required for neutralisation 4'85 c.c. Nj 10-KOII. Neutral- isation Value = 256. C12H1503N requires C = 65'2; H = 6‘8 per cent. Neutralisation Value = 254. * 2 -A-Xylylsuccinamic acid is readily soluble in alcohol, but only moderately so in chloroform, benzene, or hot water. Its methyl ester, prepared bj' heating the substance for about fifteen minutes * with methyl alcohol saturated with hydrogen chloride, crystallises from a mixture of benzene and light petroleum in colourless needles melting at 107°. Found: 0=66-7; H = 7'2. C]3TI1703N requires C = 66'4; II = 72 per cent. Action of Sodium Ethoxide on 2 : k-Xylylsuccinamic Acid. Formation of /3-2 : A-Xylylprojnonic Acid. The object of this experiment was to ascertain whether 2:4-xylyl- succinamic acid could be converted into an indole derivative accord- ing to the following scheme: Me Me V >nh-co-cii2-ch2-co2h ,-C H Me/ ^NH VbCH2-CH2-C02H. Fifty grams of the acid, in convenient portions of 10 grams each, were added to an equal weight of sodium ethoxide in a capacious flask, and the mixture heated for a short time (fifteen minutes) at a temperature of about 300° in the absence of air. The dark- coloured solid thus obtained was digested with water, and the alkaline mixture extracted with ether, which removed some xylidme and a small quantity (3 grams) of a neutral oil. The alkaline liquid was next filtered from some insoluble resin, and then acidified with dilute hydrochloric acid, when a considerable quantity of acidic substance was precipitated. The mixture was extracted with ether, the ethereal solution being washed, dried, and the solvent removed. The residue thus obtained was found to contain a large proportion of unchanged 2:4-xylylsuccinamic acid, which * Prolonged heating of this mixture causes hydrolysis, with the formation of xylidine and succinic acid.