A’-Phenylanthranilic acid

In a 500-cc. round-bottomed, flask fitted with a water-cooled condenser, 50 g. (0.23 mole) of A-phenylanthranilic acid (Org. Syn. 19, 6) [or 46 g. acridone (Org. Syn. 19, 7)] is mixed with 160 cc. (270 g., 1.76 moles) of phosphorus oxychloride (Note 1). The mixture is slowly heated (about fifteen minutes) to 85-90° on a water bath. A vigorous reaction sets in, and the flask is removed il once from the hot bath. If the reaction becomes too violent, I lie llask is immersed in a beaker of cold water for a moment. Alter live to ten minutes, when the boiling subsides somewhat, I lie llask is immersed in an oil bath. The temperature of the bath is I lien raised to 135-140°, where it is maintained for two hours. The excess phosphorus oxychloride is removed by distillation from an oil bath at M0 150° under a vacuum of about 50 mm. The residue, after cooling, is poured into a well-stirred mixture of... 

The A-phenylanthranilic acid may be used without recrystallization if it has been prepared from purified o-chlorobenzoic acid. If not, the crude A-phenylanthranilic acid must be submitted to the decolorizing treatment described in Note 4, as otherwise a greenish acridone is obtained, which, however, has the same melting point. 

A number of transition metals can be determined conveniently if their cations undergo a definite change of oxidation state see Oxidation Number) on titration with a standard solution of potassium permanganate, potassium dichromate, cerium(IV) sulfate, or ammonium hexanitratocerate(IV). Several visual indicators have been proposed, including diphenylamine and its derivatives, xylene cyanole FF, and especially A-phenylanthranilic acid and tris(l,10-phenanthroline)iron(II) sulfate ( ferroin ). Solutions of have been used in the determination of iron, copper, titanium, vanadium, molybdenum, tungsten, mercury, gold, silver, and bismuth, and standard solutions of and Sn F U, and and Mo have also... 

The coupling of A/ -phenylanthranilic acids with alkynes also proceeds smoothly accompanied by decarboxylation (Scheme 4.32) [37]. In this reaction, the combination of [RhCl(cod)]2 (cod = cyclooctadiene) and l,2,3,4-tetraphenyl-l,3-cyclopentadiene was found to be the most effective catalyst system. This reaction... 

Dioxime, in B-00285 Bromocresol green, B-00498 3-Nitro-A-[(3-nitrophenyl)sulfonyl] benzenesulfonamide, N-00115 A-Phenylanthranilic acid Et ester, in P-00089... 

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