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filingDate 1938-02-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1939-10-31-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-514103-A
titleOfInvention Improvements in and relating to the preparation of hippuric acid derivatives
abstract 514,103. Hippuric acid derivatives. GLAXO LABORATORIES, Ltd., BLOUNT, B. K., and RESUGGAN, J. C. L. Feb. 26, 1938, No. 6167. Sample furnished. [Class 2 (iii)] 4-Hydroxy-3:5-diiodo-hippuric acid is prepared by condensing an acyl derivative of p-hydroxy benzoic acid halide with glycine, removing the acyl group and iodinating the resulting phydroxy-hippuric acid with or without previous isolation of the reaction product. Iodinating agents specified are iodine, iodine and caustic soda, iodine chloride or a mixture of sodium iodate and sodium iodide. The condensation is preferably carried out in the presence of a basic substance. The product may be treated with suitable acylating, alkylating, or substituted alkylating agents and are useful in pyelography. In the examples : (1) p-acetoxy benzoic acid chloride is condensed with glycine in the presence of caustic soda and the resulting p-hydroxy-hippuric acid was crystallized and then treated with iodine in caustic soda solution yielding 4-hydroxy-3:5-diiodo-hippuric acid; (2) 3:5-diiodo-4-hydroxy-hippuric acid is treated with acetic anhydride in caustic soda solution yielding 4-acetoxy-3:5-diiodo-hippuric acid ; (3) 3:5-diiodo-4-hydroxy-hippuric acid is treated with dimethyl sulphate in caustic soda solution yielding 3:5-diiodo-4-methoxy-hippuric acid. A sample furnished under Sect. 2 (5) comprises 4-carboxymethoxy-3:5-diiodo-hippuric acid prepared by treating 4-hydroxy-3:5-diiodo-hippuric acid (prepared as in example (1) with chloracetic acid in the presence of caustic soda.
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