The electrolytic reduction of pheno- and naphtho-morpholones / by Frederic H. Lees and Frank Shedden.

  • Lees, F. H. (Frederic Herbert)
Date:
[1903.]
Catalogue details

Licence: In copyright

Credit: The electrolytic reduction of pheno- and naphtho-morpholones / by Frederic H. Lees and Frank Shedden. Source: Wellcome Collection.

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    0*1142 gave 0*3107 C02 and 0*0736 H20. C = 74*2 ; H = 7*2. C13H14(C2H302)N requires C = 74*l ; H = 7*0 per cent. Its solution in absolute alcohol gives with ferric chloride a green coloration, a similar colour change being produced by adding sodium nitrite to a solution of the ester in dilute hydrochloric acid. Action of Oxidising Agents.—When W-methylethyl-a-amino-/?- naphthol is shaken in the cold with aqueous solutions of mild oxidising agents such as ferric chloride, potassium ferricyanide, and silver nitrate, it is readily decomposed, yielding /3-naphthaquinone and methylethylamine, the latter being isolated and identified by means of its acid oxalate (m. p. 152—153°): 0*1243 gave 0*1849 C02 and 0*0848 H20. C = 40*6 ; H = 7*6. C3H9N,C2H204 requires C = 40*3 ; H = 7*4 per cent. -NMethyl-p-naphthomo'i'pholine, 03) 'O ■CHf p 11 YJ-L2 10 6 N(CH3)*CH.: (a) Fractions III and IV were combined, and further fractionated under 40 mm. pressure. In this way, some methylethyl-a amino- /9-naphthol was removed, and a fraction boiling at 213—223°, was converted into the sulphocamphylate, which crystallised from water in clusters of needles. This salt, which contained one molecule of water, when slowly heated, melted at 196° : 0*4468 lost, at 110°, 0*0164 H20. H20 = 3*6. C]3H130N,C9H1405S,H00 requires H2O = 4*0 per cent. 0*4085 anhydrous salt gave 0*2201 BaS04. S = 7*4. C13H130N,C9Hu05S requires S = 7*4 per cent. The salt, when finally recrystallised from a mixture of alcohol and ether, separated in glistening needles and readily yielded JV-methyl-/?- naphthomorpholine, the latter distilling at 220—222°, under 40 mm. pressure. It is a light yellow, viscid oil, having a blue fluorescence and a pleasant odour recalling that of its analogue V-methylphenomorpholine ; it is quite insoluble in caustic alkalis, and is perfectly stable on exposure to air : 0*1262 gave 0*3624 C02 and 0*0754 H20. C = 78*3 ; H = 6*6. C13H13ON requires C = 78*4; H = 6*5 per cent. Its solution in absolute alcohol gives, with ferric chloride, an intense bluish-green coloration. When sodium nitrite is added to its solution in dilute hydrochloric acid, a deep Prussian-blue colour is developed.
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