I2« — 



but not in the nucleus, for the compound is insoluble in alkali. But 

 the hydroxyl can be replaced on boiling with hydriodic acid by 

 hydrogen, whereby carvacrylamine is formed. Carvoline is therefore a 

 derivative of p-cymene, which has the amido-group in o-position to the 

 methyl. Diazotised carvoline can be combined with phenols to form 

 dyes. The amido-group can be substituted by chlorine, whereby an 

 hydroxychloride (m. p. 50 to 51 ) is formed boiling without decom- 

 position between 245 and 249 . With chromic acid mixture it is oxidised 

 to p-acetyl-o-chlorotoluene passing over with water vapour, melting 

 at 45 to 46 , and boiling at 250 to 2 54° This body has a distinct 

 ketonic character; its semicarbazone melts at 237 to 2 3 8°, its oxime 

 at 96 to 97 . The ketone could be converted by oxidation with 

 hypobromite into an acid melting at 200 to 20 1°, which therefore 

 showed the melting point of o-chloro-p-toluic acid. The following 

 graphic formulae represent all the reactions described: — 



CH 3 

 I 

 C 



CH, 



HC C = NOH 



I I 



H 2 C CH 2 + H 2 



\/ 



c 



II 



C(CH 8 ) 2 

 isocarvoxime 



HC C = NOH 



I I 



HL C C H 9 



V 



C(OH) 

 I 

 CH 



/\ 



C H„ C H„ 



CH 8 



I 

 C 



HC 



I 



HC 



C = N- 



CH 9 



+ H 2 



CH 8 

 C 



HC C:NH 



I I 



HC CH 2 



K/ 



c 



I 



C(OH) 

 CH, CH, 



CH, 

 I 

 C 



/\ 

 HC CNH 2 

 I II 



-> HC CH H 



\/ 



C 

 I 

 C(OH) 



/\ 



CH, CH, 

 carvoline (hydroxycarvacrylamine) 



CH, 

 I 

 C 



/\ 

 HC CC1 



I II 



HC CH 



X/ 



c 



I 



C(OH) 



/\ 



CH, CH, 



hydroxychloride 



