ACETO ACETIC ESTER 1 27 



COLLIE, J. NORMAN, 1891. 



J. Chem. Soc. 59 172-179. 

 Action of Heat on ^-Amidocrotonic Ester. 



When this substance is distilled a small amount of substance is 

 always left which has been found to be C IO H I3 NO 3 , the ethyl ester of 

 an acid, Cg H 9 NO 3 , which is dimethyl-pyridone-monocarboxylic acid, 



NH 

 / \ 

 CH 3 C C-CH 3 



II II 

 CO 2 HC CH 



\ / 



c 

 o 



The ester, C IO H I3 NO 3 , 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 Ci H I2 BrNO 3 ; 

 with PC1 5 it gives Cio H I2 NO 2 Cl, which can be changed into chloro- 

 lutidin boiling at 177 to 180. The acid C 8 H 9 NO 3 , melts at 257-258 

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



NH 

 / \ 

 CH 3 C CCH 3 . 



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, C 5 H 3 N (CO 2 H) 2 , was 

 obtained. 



