igoyl Wheeler — The Condensation of Chloral 105 
in clusters of fern-like crystals which decompose at 237°. 
This body is under investigation. 
T rich lore thy lidenedi-o-aminobenzo ic Acid, 
CC1 3 CH ( NHC 6 H 4 COOH) 2 . 
Five grams (2 molecules) anthranilic acid in 40cc boiling 
benzene were treated with 2.9 grams (1 molecule) chloral in 
lOcc benzene and boiled under a reflux condenser for three 
hours. During the boiling there separated 3.25 grams of the 
di-compound, melting at 164°-165°. On cooling a further 
yield of 0.6 gram was obtained. On evaporation to dryness 
the residue was found to weigh 4.0 grams and to melt at 
157°. The pure body melts at 165°. The method of Nie- 
mentowski 1 was tried and although found to be better than 
for the preparation of the mono-compound it gave a smaller 
yield than our method and a larger amount of unknown col- 
ored by-products. 
Analysis: 
0.5000 gram substance gave 0.0410 gram NH 3 (Kjeldahl). 
0.2000 gram substance gave 0.2113 gram AgCl. 
Calculated for 
C i 6 H I3 0 4 N 3 C1 3 Found 
N 6.96 6.76 
Cl 26.11 26.10 
The di-compound consists of a crystalline powder and may 
be purified by precipitating its ether solution with ligroin. 
Upon boiling eight hours with acetic anhydride and cooling, 
a crystalline substance deposits, melting at 183° and crystal- 
lizing from benzene in needles. This corresponds to acetyl- 
o-aminobenzoic acid. On treating a glacial acetic acid 
solution with bromine there is almost instantly obtained a 
heavy precipitate which after recrystallization from glacial 
acetic acid melts with decomposition at 236°. This behavior 
is surprisingly like that of the bromo derivative of the mono- 
anthranilic acid compound. 
1 (Ber. 35, 3898). 
