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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    acetic acid, melted at 185°. On recrystallisation from acetic acid, it separated in short, flattened, yellow prisms which melted at 188—189°. The yield amounted to 80 per cent, of the /3-naphthoxyacetic acid employed : 0-1148 gave 0*2458 C02 and 0*0372 H20. C = 58*4; H = 3*6. C12H905N requires C = 58*3 ; H = 3*6 per cent. In order to prove that the direct nitration of /3-naphthoxyacetic acid led to the production of the a-nitro-compound, a-nitro-/?-naphthol (Sten- house and Groves, Annalen, 1877,189, 151), prepared from the a-nitroso- compound (Groves, Trans., 1884, 45, 295), was condensed with chloroacetic acid by boiling an aqueous solution of their respective potassium salts in molecular proportion, for several hours. The hot aqueous liquid was then decanted from some a-nitro-/?-naphthol, which had separated owing to a side reaction, concentrated considerably, and,, while still hot, acidified with concentrated hydrochloric acid. The nitro-acid then crystallised out, and after recrystallisation from acetic acid melted at 188—189°. It was in all respects identical with tho acid prepared according to the foregoing method. 03) fi-Naphthomorpholone, C10H6<^ O—CH, NH-CO or C 10 (a) 03) h6<0,(?H2 • 6^n:c-oh (a) a-Nitro-/3-naphthoxyacetic acid (100 grams) was dissolved in hot glacial acetic acid (400 c.c.) and a quantity of boiling water (200 c.c.) added. This was followed by the cautious addition of iron filings (80 grams) to the hot solution. When the reaction became too vigorous, it was checked by placing the flask in water for a moment, the reduction being completed by heating on the water-bath for an hour. The mixture, after dilution with an equal volume of water, was cooled and filtered. The precipitate contained the /3-naphthomorpholone, mixed with a considerable amount of iron acetate which was removed by suspending the precipitate in a 20 per cent, solution of caustic soda, adding hot alcohol (500 c.c.), boiling for a short time, and filtering. The filtrate, when concentrated by distillation, diluted with water, and acidified with hydrochloric acid, deposited the /3-naphtho- morpholone in a nearly pure state, the yield amounting to 80—90 per cent, of the theoretical. On recrystallisation from acetic acid, the compound formed fine, glistening needles which melted at 215—216°: 0*1142 gave 0*3026 C02 and 0*0472 H20. C = 72*3 ; H = 4*6. C12H902N requires C = 72*4 ; 11 = 4*5 per cent. /3-Naphthomorpholone closely resembles its analogue, phenomorpho-