[3] Ber. 8, 17 (1875).

[4] Ber. 7, 1169 (1874); 10, 858 (1877).

[5] Ber. 12, 329 (1879); Ann. chim. phys. (6) 1, 461 (1884).

[6] Ber. 32, 1910 (1899).

[7] Ber. 32, 1563 (1899).

[8] Ber. 43, 3093 (1910).



XII

METHYL RED

(_o_)HO2CC6H>4s>NH2 + HNO2 + HCl-->(_ o_)HO2CC6H4N2Cl + H2O
(_o_) HO2CC6H4N2Cl + C6H5N(CH3)2-->(_ o_)HO2CC6H4N = NC6H4N(CH3)2 + HCl

Prepared by H. T. CLARKE and W. R. KIRNER. Checked by ROGER ADAMS
and J. B. DAVIS.

1. Procedure

TECHNICAL anthranilic acid (generally about 95 per cent pure)
(685 g.) is dissolved in 1.5 l. of water and 500 cc.
of concentrated hydrochloric acid (sp. gr. 1.17), by heating.