[5] Ann. 308, 265 (1899); 342, 220 (1905).

[6] Jahresb. 1876, 308; Gazz. chim. ital. 22 (2), 67
(1892); Bull. soc. chim. (3) 25, 309 (1901).

[1b] Ber. 39, 4146 (1900).

[2b] Ber. 31, 1023 (1898).

[3b] J. Am. Chem. Soc. 44, 425 (1922).



XIX

PHENYLHYDRAZINE

C6H5NH2<.>HCl + NaNO2 + HCl--> C6H5N2Cl + NaCl + 2H2O C6H5N2Cl
+ 4H(Na2SO3)--> C6H5NHNH2<.>HCl

Prepared by G. H. COLEMAN. Checked by J. B. CONANT and H. R. THOMPSON.


1. Procedure

IN a 12-l. round-bottom flask, fitted with a mechanical stirrer,
are placed 1045 cc. of concentrated commercial hydrochloric acid
(sp. gr. 1.138). The flask is surrounded with a freezing mixture
of ice and salt, and when the contents are at 0'0, stirring is started
and 500 g. of cracked ice are added; then 372 g. of aniline,