pared by benzoylation of 5-amino-8-hydroxyquinoline showed no depression. Moreover, by hydrolysis with hydrochloric acid (20%) the formation of benzoic acid could be ascertained by the mixed melting point method.Anal. Subs., 3.066: N2, 0.290 (24°, 766 mm.). Caled, for CieHuO«Ni: N, 10.61. Found: N, 10.63. Acid sulfate gave yellow columns from alcohol; m. p. 221-222°( decomp.). 8-Benzoyloxyquinoline.-The benzoylation of 8-hydroxyquinoline with benzoyl chloride was carried out in the presence of pyridine in the cold; yield, 90% of the theoretical after recrystallization. It forms in colorless tables from alcohol; m. p. 122-122.6°.This compound was prepared first by Bedall by the interaction of 8-hydroxyquinoline and benzoyl chloride at a high temperature; he found a melting point of 118-120°f or his product.8Anal. Caled, for CisHuOíN: N, 6.62. Found: N, 5.64.The hydrochloride was obtained by treating an ice cold ethereal solution of the free base with dry hydrogen chloride gas. It forms in colorless needles; m. p. 124°. It is easily soluble in water.Anal. Caled, for C16HnOiN-HCl: HC1, 12.78. Found: HC1, 12.64. On submitting this hydrochloride to a Friedel and Crafts reaction, benzoic acid and 8-hydroxyquinoline could be recovered and no condensation product could be isolated.I hereby desire to express my hearty thanks to Professor Hata for the interest which he has kindly taken in this work and to Mr. C. Sone for his assistance in this investigation.
SummaryThe preparation of 5-acetyl-, 5-chloro-acetyl-and 5-benzoyl-8-hydroxyquinoline has been reported.Tokyo, Japan
iodide and picrate, tri-p-tolylselenonium chloride and iodide, di-m-tolyl selenide, di-m-tolyl selenium dichloride, tri-m-tolylselenonium iodide and tri-?M-tolylselenonium chloride-mercuric chloride.3. Triphenylselenonium hydroxide has been prepared in dilute solution. The solution when concentrated decomposes into benzene (?) and diphenyl selenium oxide.4. The formation of triphenylselenonium chloride by fusing di-p-tolyl selenide with mercury diphenyl and the thermal decomposition of diphenylp-tolylselenonium iodide into phenyl iodide and phenyl p-tolyl selenide indicate the p-tolyl group to be more negative than the phenyl.
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