patents referred to. It seems, however, not out of place to call attention to the reaction as worked out by Dr. Warren and the writer, since Dr. Dunlap seems to have overlooked its general R. W. CORNELISON. nature. BLOOMFIELD, N. J., THE JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. VOL. XXIV.-NO. 11. NOVEMBER, 1902. WILLIAM A. NOYES, Editor, EDWARD HART, W. F. HILLEBRAND, J. H. LONG, WM. MCMURTRIE, ARTHUR A. NOYES, EDGAR F. SMITH, H. N. STOKES, H. P. TALBOT, H. W. WILEY. The Synthesis of Alkylketodihydroquinazolines from Anthranilic Ni- On the Reduction of Sonie Aromatic Nitro-Compounds. way and M. D. Welsh... 1050 By F. J. Al 1052 1060 On the Nitration of Benzyl Chloride. By Frederick J. Alway 1063 1066 1068 Arsenic Pentachloride. By Charles Baskerville and H. H. Bennett... 1070 1073 The Use of Potassium-Ferric Chloride for the Solution of Steel in Ma- 1076 1080 1082 The Quantitative Determination of Selenium in Organic Compounds. 1087 The Determination of Sulphur and Phosphorus in Plant Substances. 1093 The Determination of Sulphur and Phosphorus in Organic Materials. 1100 Further Notes on the Bromine Absorption of Oils. By Parker C. McIlhiney The Analysis of Vanilla Extract. By A. L. Winton and M. Silverman 1128 Creaming of Milk During Its Sale. By William Frear and M. H. Pingree 1136 NEW BOOKS: On Cane-Sugar and the Process of Its Manufacture in Java; The Gas Engineer's Laboratory Handbook; Guide to Preparation Work in Inorganic Chemistry 1138 REVIEW OF AMERICAN CHEMICAL RESEARCH. .... 481-520 Entered at the Post-office, Easton, Pa., as Second-class Matter. Everything intended for insertion in the Journal should be addressed to the Editor, William A. Noyes, Terre Haute, Ind. Orders for back numbers of the Journal should be addressed to the Librarian, E. G. Love, 108 West 55th Street, New York City. Changes of address should be sent to the Secretary, A. C. Hale, 352 A Hancock Street, Brooklyn, N. Y. President: Ira Remsen, Johns Hopkins University, Baltimore, Md. Librarian: E. G. Love, 108 W. 55th St., New York City. Committee on Papers and Publications: William A. Noyes, Editor; Edward Hart, W Committee on Membership: Wm. McMurtrie; C. L. Reese; E. G. Love. Council. Members ex-officio: Ira Remsen, Pres.; Albert C. Hale, Sec.; Albert P. Hall × Councilors from Local Sections.-Rhode Island Section: Charles A. Catlin. Cincine Section: Thomas Evans. New York Section: Leo Baekeland, A. A. Breneman, C Doremus, T. J. Parker, G. C. Stone. Washington Section: W. F. Hillebrand, H Stokes. Lehigh Valley Section: P. W. Shimer. Chicago Section: J. H. Long. Nebra Section: H. H. Nicholson. North Carolina Section: B. W. Kilgore. Colum Section: Wm. McPherson. North Eastern Section: W. L. Jennings, A. D. L H. P. Talbot. Philadelphia Section: H. W. Jayne, John Marshall. Michigan Secti E. D. Campbell. Kansas City Section: J. Robt. Moeche!. California Section: [ Stillman. Local Sections. Rhode Island Section: Walter M. Saunders, Pres.; Walter E. Smith, S 158 Doyle Ave., Providence, R. I. Cincinnati Section: R. W. Hochstetter, Pres.; Snell, Sec., University of Cincinnati, Cincinnati, O. New York Section: Thoma Parker, Pres.; Francis D. Dodge, 360 Washington Avenue, Brooklyn, N. Y. Washi ton Section: W. F. Hillebrand, Pres.; L. S. Munson, Sec., Dept. of Agr., Washing D. C. Lehigh Valley Section: Joseph W. Richards, Pres.; R. K. Meade, Sec., Lafay College, Easton, Pa. Chicago Section: Edward Gudeman, Pres.; W. A. Converse, S 27-34 Rialto Bldg., Chicago. Nebraska Section: H. H. Nicholson, Pres.; R. S. Hit Sec., University of Nebraska, Lincoln, Neb. North Carolina Section: C. E. Bre Pres.; C. B. Williams, Sec., North Carolina Dept. of Agr., Raleigh, N. C. Colum Section: H. A. Weber, Pres.; W. F. Henderson, Sec., Ohio State University, Colun 0. North Eastern Section: L. P. Kinnicutt, Pres.; Henry Fay, Sec., MassachuInst. Tech., Boston, Mass. Philadelphia Section: Henry Leffmann, Pres.; F Dodge, Sec., Works of Barrett Mfg. Co., Frankford, Philadelphia. Michigan Sect E. D. Campbell, Pres.; Alfred H. White, Sec., 1003 E. University Ave., Ann Arbor, Kansas City Section: E. H. S. Bailey, Pres.; Armand R. Miller, Sec., M. T. High Sch Kansas City, Mo. California Section: Edmond O'Neill, Pres.; Harry East M.. Sec., 331 Pine St., San Francisco, Cal. PAPERS ACCEPTED FOR PUBLICATION. Some Cuban Soils of Chemical Interest. By William Frear and C. P. Beistle. Fixation of Atmospheric Nitrogen by Alfalfa on Ordinary Prairie Soil under Various Treatm By C. G. Hopkins. The Rapid Determination of Carbon by Combustion. By George Auchy. Some Notes Concerning Halphen's Test for Cotton Seed Oil. By Elton Fulmer. A Rapid Method of Separating Zinc and the Alkaline Metals from Iron. By H. C. Babbitt On Azoxybenzene. By Arthur Lachman. The Determination of Manganese in Iron and Steel. By John V. R. Stehman. The Solubility-Equilibrium between Silver Chloride and Solutions of Potassium Chlorid: Hydroxide. By A. A. Noyes and D. A. Kohr. A Contribution to the Chemistry of Fatigue. By H. W. Harper and Margaret Holliday. Note: Filtration in Determinations of Crude Fiber. By R. W. Thatcher. On the Fixation of Ammonia and Potash by Hawaiian Šoils. By J. T. Crawley. A Probable Cause of the Different Colors of Iodine Solutions. Derivatives of Phenyl Ether, V. By Alfred N. Cook. By Arthur Lachman. An Investigation of Ammonio-Silver Compounds in Solution. By W. R. Whitney and A Melcher On the Composition of Cow's Milk. By H. C. Sherman. The Alkaloids of Isopyrum and Isoproine. By G. B. Frankforter. Copyright, 1902, by William A. Noyes, Chairman of the Committee on Papers and Publications of the [CONTRIBUTION FROM THE HAVEMEYER LABORATORIES, COLUMBIA UNIVERSITY, No. 70.] THE SYNTHESIS OF ALKYLKETODIHYDROQUINAZOLINES FROM ANTHRANILIC NITRILE.1 BY MARSTON TAYLOR BOGERT AND WILLIAM FLOWERS HAND. Received July 31, 1902. THEORETICAL PART. Bogert and GOTTHELF have already shown2 that ketodihydroquinazolines may be prepared by heating together in sealed tubes anthranilic acid, or its acyl derivatives, with a nitrile, and the reactions there suggested in explanation of this synthesis, taking the case where an acylanthranilic acid was the starting-point, were as follows: It will be seen upon examining the structure of the hypo 1 Read before the New York Section of the American Chemical Society, at its meeting January 24, 1902. 2 This Journal, 22, 129 and 522; 23, 611. thetical intermediate product, the secondary amide, that the -CO-NH-CO-group being symmetrical should be formed equally well from RCN+R'.COOH as from R'CN+R.COOH; in other words, as the condensation takes place solely between the CN and COOH it is immaterial which radical carries the CN and which the COOH. This same secondary amide should therefore result when acetylanthranilic nitrile is heated with acetic acid, as follows: At higher temperatures then, acetic acid would split off, as indicated, with production of the quinazoline body, and we have in this manner prepared a number of the quinazolines in question, the products being in every case identical with the compounds obtained from anthranilic acid already described in the articles referred to. The alkylketodihydroquinazolines may therefore be prepared either from anthranilic acid or from the corresponding nitrile. In cases where the o-amino acid is best obtained by saponification of the nitrile, it is convenient to be able to pass directly to the quinazoline from the nitrile without having to prepare the acid at all, thereby saving one step in the synthesis. We have thus prepared quinazolines from homoanthranilic nitrile. The starting-point for our work was o-nitraniline, from which o-nitrobenzonitrile was prepared by the Sandmeyer reaction, the yield being excellent. The nitronitrile can be entirely freed from precipitated mineral cyanides by crystallizing from boiling carbon tetrachloride in which the latter are insoluble. This method of purification had been worked out by one of us before the article by Friedländer1 came to our attention. The latter uses benzene as the means of separating the nitronitrile from the mineral cyanides, but we do not consider this so good a solvent as carbon tetrachloride, since the nitronitrile is much less soluble in cold carbon tetrachloride than in cold benzene, and where the latter is used much more of the compound is left the mother-liquors. The old process of puriation by distillation |