Researches on the constitution of physostigmine. Pt. I[-II] / by Arthur H. Salway.
- Salway, Arthur Henry.
- Date:
- 1912-1913
Licence: In copyright
Credit: Researches on the constitution of physostigmine. Pt. I[-II] / 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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![formed in the above reaction by the reducing action of the liberated hydriodic acid on the 3-chloroacetyl-2-methylindole. If this supposi- tion regarding the constitution of the compound melting at 197° were correct, then the same substance should be obtained by the action of acetyl chloride on magnesium 2-methylindolyl iodide. This experiment, conducted in a manner similar to that employed in the preparation of 3-chloroacetyl-2-methylindole, yielded a product identical with the above-mentioned substance melting at 197°. The latter is therefore 3-acetyl-2-methylindole. Z-A cetyl-2-methylindole is moderately soluble in chloroform or alcohol, but only sparingly so in benzene or ether. It crystallises from hot alcohol in slender’, colourless needles, and from chloroform in thin, colourless plates, melting at 197°. It does not give the pine-shaving colour reaction of indole. It yields an oxime, which crystallises from dilute alcohol in glistening leaflets, melting and decomposing at 199°: 0-0972 gave 0’2502 C02 and 0'0568 H20. C = 70‘2; H = 65. CnH12ON2 requires C = 70’2; H = 64 per cent. Z-Dimethylaminoacetyl-2-methylindole (III). A quantity of 3-chloroacetyl-2-methylindole was heated for four hours at 100° in a sealed tube with an excess of dimethylamine dissolved in alcohol. The solvent and the excess of dimethylamine were first removed in a current of steam, and the mixture then acidified with dilute hydrochloric acid, when a quantity of non- basic material remained undissolved, the latter being collected and set aside for subsequent examination. The acid liquid was now made alkaline with sodium carbonate, and the precipitated base collected, washed with water, and purified by crystallisation from alcohol. It was obtained in colourless, rhombohedral prisms, which melted at 201°. The yield of pure substance amounted to 62 per cent, of the theoretical: 0-0958 gave 0'2540 C02 and 0'0640 H„0. C = 72'3; B>74. Cj3H]0ON2 requires C = 72-2; H = 7'4 per cent. The non-basic by-product in the above reaction was very sparingly soluble in the usual organic solvents. It was crystallised, however, from much hot acetic acid, and then obtained in small, colourless, square prisms, which melted and decomposed at 270°: 0-1304 gave 0-3243 C02 and 0'0760 H20. C = 67'8; II = 6 5. 0-1980 „ 0-0640 AgCl. Cl = 8‘0. 0-1718 „ 14-4 c.c. N2 at 12° and 775 mm. N = 10'2. C24H2f,02N3Cl requires C=680; H = 61; N = 9 9; Cl = 8'4 per cent. It appears from these results and the properties of the compound](https://iiif.wellcomecollection.org/image/b2243933x_0023.jp2/full/800%2C/0/default.jpg)
