— 62 — 



P. Freundler 1 ) has discovered a suitable reaction for the 

 detection, and possibly also for the quantitative estimation, of 

 methyl ester of anthranilic acid. In a manner similar to that 

 in which H. N. Mac Coy 2 ) obtained thiophenyl ketotetrahydro- 

 quinazoline from anthranilic acid by heating it with phenyl mustard 

 oil and alcoholic soda liquor, Freundler obtained this compound in 

 a quantitative yield, simply by heating methyl ester of anthranilic 

 acid with phenyl mustard oil to ioo° to 120 . The conversion 

 takes place according to the following equation: 



COOCH3 CO-N.CH. 



/ / I 



C 8 H 4 -j-S:C:N.C 6 H 5 = C 6 H 4 CS +CH 3 OH. 



\ \ / 



NH 2 NH 



The compound melts above 300 , is readily soluble in soda liquor 

 and very difficultly in alcohol. From 5,1 gm. pure methyl ester of 

 anthranilic acid, 98°/ of the calculated quantity of quinazoline was 

 obtained. With regard to the application of the method for the deter- 

 mination of methyl ester of anthranilic acid in essential oils, for which 

 the authors propose it, no experiments are as yet mentioned. But 

 Freundler used this derivative to confirm the statements made by 

 E. von Meyer and M. Schmidt 3 ) that on heating isatoic acid with 

 methyl alcohol to 130 , methyl ester of anthranilic acid is formed. 

 E. and H. Erdmann 4 ), on applying for a patent for the manufac- 

 ture of this compound, had contested the correctness of the result ob- 

 tained by E. von Meyer and M. Schmidt, and consequently the 

 latter's priority for the synthesis of this ester. 



When repeating the experiment under the conditions mentioned 

 by E. von Meyer and M. Schmidt, E. Erdmann 5 ) was, however, 

 compelled to admit that as a matter of fact methyl ester of anthranilic 

 acid is formed. Whilst Freundler employed phenyl mustard oil for 

 the separation of methyl ester of anthranilic acid from the other pro- 

 ducts formed by the action of isatoic acid on methyl alcohol, he 

 established that at least 2 8°/o 0I tne isatoic acid employed had been 

 converted into methyl ester of anthranilic acid. We, who by the detec- 

 tion of methyl ester of anthranilic acid in neroli oil and other blossom 

 oils, and also by the technical application of the synthetic ester were 

 the first to demonstrate the importance of the compound as an odorous 

 substance, have from the beginning admitted the identity of that body 



*) Bull. Soc. Chim. III. 31 (1904), 882. 



2 ) Berl. Berichte 30 (1897), 1688. 



3 ) Journ. f. prakt. Chem. II. 36 (1887), 374. 



4 ) German Patent No. 1 10386, cl. 12; March 16, 1900. 



5 ) Berl. Berichte 32 (1899), 2168. 



