RECENT WORK ON THE MORPHINE GROUP 289 



corresponding amino-acid and diazotised. The diazo-body was 

 then treated with dilute sulphuric acid, which caused nitrogen 

 and water to split off, torming 3, 4-dimethoxy-phenanthrene-9- 

 carboxylic acid, and by distillation the latter was resolved into 

 carbon dioxide and dimethoxyphenanthrene : 



CH 3 



CHO CH.COOH 



+ 



CH 



CH 3 k^N0 2 

 OCH3 



C.COOH 



CH3O 



H 

 C 



^/NNOH 

 OCH, 



C.COOH 



CH 



COOH 



CH.O 



Under the well-known conditions of this reaction, it is certain 

 that the methoxyl groups must be in positions 3 and 4 respec- 

 tively, and this synthetic body is identical with the dimethyl- 

 morphol prepared by Vongerichten : from methylmorphol. 



Following on similar lines, Pschorr and Vogtherr 2 have 

 prepared acetylmethylmorpholquinone by condensing vic.o- 

 nitroz'sovanillin with phenylacetic acid. The resulting product 

 was then converted into the diazo-compound as before, and 

 finally into 3-methoxy-4-hydroxyphenanthrene-9-carboxylic acid, 

 which was acetylated and afterwards oxidised by means of 

 chromic acid, whereby 3-methoxy-4-acetoxyphenanthraquinone 

 was obtained : 



CH3O 



CH 3 C0.0 



This proved to be identical with the acetylmethylmorphol- 

 quinone prepared by Vongerichten 3 from morphine. 



1 Ber. 33, 1824. 



Ibid. 35, 4412. 



Ibid. 31, 52. 



19 



