PREPARATIONS 217 TV-Phenylanthranilic Acid, C 6 H 5-NH-C n H 1-COOH. (The Ullmann Condensation.) A halogen atom directly attached to a benzene ring is usually unreactive, unless it is activated by the nature and position of certain other substituent groups. It has been shown by Ullmann, however, that halogen atoms normally of low reactivity will condense with aromatic amines in the presence of an alkali carbonate (to absorb the hydrogen halide formed) and a trace of copper powder or oxide to act as a catalyst. This reaction, known as the Ullmann Condensation, is frequently used to prepare substituted dipheny !amines: it is exemplified O COOH in the following condensation of o-chlorobenzoic acid \vith aniline to give N-phenylanthranilic acid or o-carboxydiphenylamine. Required: Aniline, 30 ml.; o-chlorobenzoic acid, 8 g.; potas-sium carbonate, 8 g.; powdered copper oxide, 0-4 g. Prepare a mixture of 30 ml. of aniline, 8 g. of o-chloro-benzoic acid, 8 g. of anhydrous potassium carbonate and 0-4 g.
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This note was uploaded on 09/19/2011 for the course CHM 2211 taught by Professor Castalleano during the Fall '06 term at University of Florida.