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

  • Salway, 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.

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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    VITRO-GROUP IN NITROMYRISTICINIC ACID. Ethyl Nitrorwyristicvnate {Ethyl 2-Nitro-Z-methoxyA: 5-methylene- dioxybenzoate), III, p. 267. Twenty grams of ethyl myristicinate (b. p. 193°/20 mm.) were lidded gradually at 0° to 200 c.c. of concentrated nitric acid 'D T41). The mixture was kept in the cold for an hour, and then loured into ice-water, when an oil was precipitated, which gradually iolidified. This was collected, washed free from nitric acid, and Durified by recrystallisation from alcohol. The compound was thus nbtained in stout, colourless prisms, melting at 82°: 04019 required for saponification 15-05 c.c. N/ 10-NaOH. Saponification value = 210-1. CnHn07N requires saponification value=208‘6. Ethyl nitromyristicinate is colourless when freshly prepared, but gradually becomes yellow on exposure to light. When hydrolysed, it yield a mononitromyristicinic acid, which was proved to be identical with the acid derived by the direct nitration of myristicinic acid. Ethyl Aminomyristicinate [Ethyl 2-Amino-2-me.thoxy- 4: 5-methylenedioxybenzoate), IY, p. 267. For the preparation of this compound, one part of ethyl nitro- myristicinate was cautiously heated with tin (one part) and an excess of concentrated hydrochloric acid. After the vigorous reaction had subsided and the nitro-ester had completely dissolved, the mixture was poured into a large volume of water, when the greater portion of the amino-ester was precipitated as an oil, which soon became solid. This was collected, washed, and purified by recrys- tallisation from alcohol. A further quantity of the amino-ester was obtained from the acid filtrate by rendering it alkaline and extracting with ether: 0-1114 gave 0’2250 C02 and 0 0546 H20. C = 55'l; H = 5‘4. CnH]305N requires C=55'2; H = 54 per cent. Ethyl aminomyristicinate crystallises from alcohol in colourless, prismatic needles, melting at 93°. Its ethereal solution possesses a blue fluorescence. It is a very weak base, being precipitated from its solution in concentrated hydrochloric acid by the addition of water. When hydrolysed, it yields aminomyristicinic acid, which crystallises from alcohol in long, slender, colourless needles, melting and decomposing at 200°. Solutions of the latter substance also show a blue fluorescence: 01190 gave 0-2239 CO, and 0’0480 H„0. C = 513; H = 45. C0H9O5N requires C = 51'2; H = 4‘.'i per cent.