igoy ] Wheeler — The Condensation of Chloral 99 
chlor-4-nitraniline do not react. Wheeler and Weller 6 pre- 
pared the o- and m-nitraniline compounds and Wheeler and 
Daniels 7 showed that only addition products could be obtained 
with the naphthylamines. Niementowski and Orzechowski 8 
found that one molecule of chloral condensed with one mole- 
cule of anthranilic acid but later 9 obtained the expected 
diphenamine compound. Finally Rugheimer 10 describes the 
compounds with o- and p-phenylenediamine and 1, 2, 4- and 
1, 3, 4-toluylenediamine. He also states that only addition 
products are obtained with the naphthylamines. 
The chloral diphenamine compQunds vary considerably in 
stability. Most of them may be kept for years. They pos- 
sess great crystallizing power. Their behavior toward 
alkalies is variable. The aniline derivative is decomposed 
by alcoholic potash into aniline, chloroform and phenyl cya- 
nide according to Wallach. The p-nitraniline derivative is 
converted by alcoholic potash into an hydroxy compound, one 
chlorine being replaced by the hydroxyl group according to 
Wheeler and Glenn 1 . They are not stable in the presence of 
strong mineral acids. These split the compound so as to re- 
form the amine. Eibner has shown that boiling acetic anhy- 
dride and benzoyl chloride give the acetyl or benzoyl deriva- 
tive of the original amine. I have found that all of them 
react with great readiness with bromine in the cold. There 
is a substitution of one hydrogen atom in those which have 
been analyzed. This substitution probably occurs in the 
methylene group of the chloral residue. 
With the exception of the anathranilic acid products the 
following are thought to be new. 
6 (Jr. Am. Chein. Soc. 24, 1063). 
7 [Jr. Elisha Mitchell Sci. Soc. 22, 90 (1906). 
8(Ber. 28, 2812). 
»(Ber. 35, 3898). 
lO(Ber. 39, 1653). 
!(Jr. Elisha Mitchell Sci. Soc. 19, 63, 1903). 
