The reduction of hydroxylaminodihydroumbelluloneoxime / by Frank Tutin.
- Tutin, Frank.
- Date:
- 1907
Licence: In copyright
Credit: The reduction of hydroxylaminodihydroumbelluloneoxime / by Frank Tutin. 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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![0'4086 dissolved in 25 c.c. of Avater gave an - 0° 26' in a 2-dcm, tube, whence [a]n - 13-25° The specific rotatory power of the base, calculated from that of the dihydrochloride is [a]o — 18-8°. Aminoletrahydrouinhellulylamine dihydrochloride dissolves in water with great readiness ; it is moderately soluble in alcohol, and almost insoluble in ethyl acetate. In a mixture of ethyl acetate and alcohol it dissolves more readily in the cold than when heated. Aminotetrahydroumhellulylamine Dibenzoate, C^oH22^2’^^7^o^2-— an aqueous solution of the base, a slight excess of benzoic acid was added, and on evaporation in a vacuum over sulphuric acid a hard crystalline mass Avas obtained. This was dissolved in boiling alcohol, and the liquid concentrated, after which the salt separated in colourless prisms which melted at 212—213°, and this melting point was not altered by further crystallisation : 0-1042 gave 0-2660 and 0-0755 HgO. C = 69-6; H = 8-l. CioH2oN2,2C7Hg02 requires C = 69-9 ; H = 77 per cent. CioH22N2,2C7Hg02 „ 0 = 69-5; H = 8-2 „ „ The optical rotation of the dibenzoate was determined in Avater and in absolute alcohol. 0 4244, dissolved in 25 c.c. of absolute alcohol, gave ud — 0° 18' in a 2-dcm. tube, whence [a]o—8-83°. 0-4244, dissolved in 25 c.c. of watei-, gave ao-0° 15' in a 2-dcm. tube, whence [a]D-7'36°. The specific rotation of the base, calculated from that of its dibenzoate, is [a]n - 17-9°. A quantity of the dibenzoate was fractionally crystallised from alcohol, but all the crops of crystals obtained were indentical and had a uniform melting point of 212—213°. Dihenzoylaminoietro.hydroumbelhdylamine, CjoH2QN2(CO*CgH5)2.— The base obtained from either the pure dibenzoate or the pure dihydrochloride, when benzoylated by means of the Schotten-Baumann method, gave a product Avhich, Avhen crystallised from alcohol, melted at 194°. On fractional crystallisation this was found to be homogeneous. 0-0990 gave 0-2762 COg and 0-0691 HgO. C = 76-1 ; H = 7-8. 0-2642 „ 16-6 c.c. of nitrogen at 20° and 776 mm. N = 7-3. CioHj8N2(00-CgH5)2 requires C = 76-6 ; H = 7-4; N = 7-4 per cent. CioH2oN2(CO-CgH5)2 „ 0 = 76-2; H = 7-9; N = 7-4 „ „ The optical rotation of the dibenzoyl derivative Avas determined in chloroform solution. 0-5379, dissolved in 25 c.c. of chloroform, gaveau + 5°3' in a 2-dcm. tube, whence [a]o-f 117-3°. Dibenzoylaminotetrahydroumbellulylamine is readily soluble in chloroform and nearly insoluble in water. When crystallised from absolute alcohol, in Avhich it is moderately soluble, it separates in short](https://iiif.wellcomecollection.org/image/b22425366_0008.jp2/full/800%2C/0/default.jpg)
