ACETO ACETIC ESTER 1 27 



COLLIE, J. NORMAN, 1891. 



J. Chem. Soc. 59, 172-179. 



Action of Heat on ^9-Amidocrotonic Ester. 



When this substance is distilled a small amount of substance is 

 always left which has been found to be Cio H13 NO3, the ethj^l ester of 

 an acid, Cg Hg NO3, which is dimethyl-pyridone-monocarboxylic acid, 



NH 

 / \ 



CH3C C-CH3 



II II 

 CO2 HC CH 



\ / 

 C 



o 



The ester, Cio H13 NO3, melts at 163^-164° and boils with slight decom- 

 position at 240° to 250° It does not form a compound with phenyl- 

 hydrazin or hydroxylamin. With bromin it forms CioHi2BrN03; 

 with PCI5 it gives Cio H12 NO2 CI, which can be changed into chloro- 

 lutidin boiling at 177° to 180° The acid Cg H^ NO3, melts at 257°-258° 

 and is converted into «-a'-dimethyl-pyridone, 



NH 



/ \ 



CH3 C CCH3 



I I 

 HC CH 



\ / 

 CO 



This was also prepared from dehydracetic acid. Phosphorus penta- 

 chlorid acts on a-a'-dimethyl-pyridone to' form chlorolutidin boiling at 

 1 78°- 1 79.° a-a'-Dimethyl-pyridin or lutidin was obtained in four ways, 

 (i) by the action of nascent hydrogen on chloroludidin ; only a little 

 could be formed in this way ; (2) from vapors of chlorolutidin and zinc 

 dust in an atmosphere of hydrogen ; (3) from chlorolutidin made from 

 dehydracetic acid ; (4) from the potassium salt of lutidone-mono. 

 carboxylic acid heated with an excess of solid potassium hydroxid. 

 By oxidation of the lutidin, dipicolinic acid, C5 H3 N (CO2 H)2, was 

 obtained. 



