X88 The Philippine Journal of Science ms 



ACTION OF PHENYLHYDRAZINE ON PHTHALOXIME 



When an alcohol solution of either the white or yellow phthal- 

 oxime is gently warmed with phenylhydrazine, the following 

 reaction takes place: 



/C=0 /C^OH 



C 6 H 4 \) -fH 2 NNHC 6 H 5 -> C 6 H 4 



^C=NOH ^c€ 



\NHNHC 6 H 5 



Phthaloxime. Anilidophthalamic acid. 



The anilidophthalamic acid thus formed was recrystallized 

 from alcohol until colorless, and found to be identical with the 

 compound described by Hotte 2T who obtained it from phthalic 

 anhydride and phenylhydrazine. 



0.1698 gram gave 17.2 cubic centimeters nitrogen over water at 31°. 5; 

 barometer, 763 millimeters. 



Calculated for t?„,,„ a 



Nitrogen 10.93 10.96 



0.1974 gram dissolved in absolute alcohol required 7.70 cubic centimeters 

 of N/10 sodium hydroxide for neutralization. Theory, 7.71 cubic centi- 

 meters. 



The absorption spectrum of anilidophthalamic acid is plotted 



in fig. 6, and indicates by the band heading at t-=3700 that 



the structure is analogous to phthalhydroxamic acid and correctly 

 represented by the above formula. 



PHTHALYLPHENYLHYDRAZINE 



If the alcohol solution of phthaloxime and phenylhydrazine be 

 heated on the water bath for an hour, the reaction proceeds fur- 

 ther with the splitting off of one molecule of water. A neutral 

 yellow compound is formed identical with Hotte's phthalylphenyl- 

 hydrazine. The same product results when anilidopthalamic 

 acid is heated, the reaction going to completion rapidly at 100°. 

 This compound crystallizes from alcohol in long yellow prisms, 

 and melts at 182° uncorrected. 



(1) 0.1854 gram gave 20.0 cubic centimeters nitrogen over water at 29°; 

 barometer, 762.5 millimeters. 



(2) 0.1740 gram gave 18.8 cubic centimeters nitrogen over water at 30°; 

 barometer, 763.7 millimeters. 



(3) 0.2230 gram gave 0.5761 gram C0 2 and 0.0821 gram H 2 0. 



27 Journ. f. prakt. Chem. (1887) , II, 35, 268. 



