2 AKT. 17. K. MATSUBAKA : FORMATION OF 



in alcoholic solution with tin and hydrochloric acid ; by Camps 

 (D. R. P., 1898, 102894 ; Ber., 1899, 32, 3228 ; Arch. Pharm., 

 1899, 237, G90; 1901, 239, 601) by treating an absolutely dry 

 solution of ethyl acetanthranilate in toluene with metallic sodium, 

 and also by boiling o-acetophenyl urethane with an aqueous 

 alcoholic solution of caustic soda for several hours. Erdmann 

 (Ber., 1899, 32, 3570) obtained it by the action of metallic 

 sodium on a mixture of ethyl anthranilate and ethyl acetate, 

 ethyl acetanthranilate which is first formed giving off alcohol 

 spontaneously or more easily on acidification. The Badische 

 Anilin- und Soda-Fabkik (D. R. P., 1900, 117167) patented 

 a method of preparing it by heating an alkali or alkaline earth 

 salt of acetanthranilic acid with dry alkali or alkaline earth 

 to 150°. 



During the course of some experiments wdth o-nitrobenzoyl- 

 acetic acid, it was observed that this acid gave r-oxycarbostyril 

 on reduction with ferrous sulphate and ammonia. The use of 

 ferrous sulphate and an alkali as a reducing agent is not new. 

 WÖHLER in 1828 (Pogg. Ann., 13, 448) had already used ferrous 

 sulphate in presence of baryta to reduce picric acid and obtained 

 picramic acid. Baeyer and Bloem (Ber., 1882, 15, 2147) 

 reduced ethyl o-nitrophenylpropiolate by pouring its solution in 

 ammonia into a saturated solution of ferrous sulpliate, and ob- 

 tained ethyl o-aminobenzoylacetate. Many other examples of the 

 application of this salt with one or other alkali as a reducing 

 agent can be found in the literature of the subject. 



o-Nitrobenzoylacetic acid was prepared according to the 

 method described by Needham and Perkin (Jour. Chem. Soc, 

 1904, 85, 148). After recrystallising from benzene, in which 



