MarcH 8, 1912] 
Nitration of 2-methyl-3-phenyl-4-quinazolone 
with a mixture of concentrated sulfurie and 
fuming nitrie acids gives a dinitro derivative; by 
similar treatment of 2-methyl-3-p-nitrophenyl-4- 
quinazolone, only one nitro group is introduced; 
but these two dinitro derivatives are not identical. 
Nitration of 2-methyl-3-p-tolyl-4-quinazolone also 
gives a dinitro derivative. The action of nitric 
acid, in presence of metallic mereury, upon 2- 
methyl-4-quinazolone gives only the mercury salt 
of the latter, whereas with quinoline a nitro- 
hydroxy derivative is produced. 
The 4-quinazolones are not readily brominated, 
but by the Juvalta process bromine derivatives 
may be obtained. 
M. T. BocErt and G. A. GEIGER: On Quinazolone 
LIodomethylates. 
Todomethylates, and other iodoalkylates, have 
been prepared from a large number of quinazo- 
lines, and the following general conclusions are 
drawn from the experiments: 
1. 4-Quinazolones. add alkyl iodides generally 
only under pressure at about 110°. 
2. The alkyl iodide adds to the N adjacent to 
the benzene nucleus (7. é., the N in position 1 in 
the quinazoline nucleus) and not to the N in posi- 
tion 3, since the compounds obtained by adding 
methyl iodide to 2-methyl-3-ethyl-4-quinazolone and 
ethyl] iodide to 2, 3-dimethyl-4-quinazolone are not 
identical. 
3. The iodoethylates are more soluble in water, 
and in methyl alcohol, than the iodomethylates. 
4. By the action of methyl iodide alone, in ex- 
cess, 4-quinazolone, 3-methyl-4-quinazolone and 4- 
methoxyquinazoline, all give one and the same 
product, namely, the iodomethylate of 3-methyl-4- 
quinazolone. 
5. Many of the nitro 4-quinazolones refuse to 
combine with methyl iodide. 
6. Styryl 4-quinazolones add methyl iodide more 
readily than ethyl iodide, but certain groups in 
position 3 appear to prevent the combination even 
with methyl iodide. 
7. By the action of silver nitrate upon some of 
these iodomethylates, corresponding methyl nitrate 
addition products have been obtained. 
M. T. Bocert and L. E. WIsE: On p-Aminobenzo- 
nitrile. (Third paper.) 
The following additional compounds have been 
prepared and studied: p-aminobenzonitrile picrate, 
p-cyanoxanilamide, oxanilic p-cyananilide, p-eyan- 
succinanilie acid, its silver salt, methyl and ethyl 
SCIENCE 
' considerable difficulty 
387 
esters, and anil, p-cyanphthalanilic acid and its 
anil, p-cyanphenylurethane, p-caramido phenyl- 
urethane, p-cyanphenyl urea, carbanilic p-cyananil- 
ide, p-cyancarbanilide, methylene di(p-cyanphena- 
mine), 3-nitro-4-acetamino benzamide and 3, 4-di- 
acetyldiaminobenzonitrile. 
The nitrile appears to add a molecule of chloral 
directly, and then on dehydration gives the trichlo- 
tethylidene di-p-cyanphenamine. 
Bromination of the acetamino nitrile, like nitra- 
tion, gives the mono substitution product. 
From 3, 4-diaminobenzonitrile, the 3-cyan-alpha- 
methyl benzimidazole can be obtained as well as 
the corresponding amide. 
M. T. Bogert and G. D. Brau: A Further Study 
of the Stilbazoles, Hydrazones and Schiff Bases 
im the 4-Quinazolone Group. 
In the condensation of aldehydes with alpha- 
methyl pyridines or quinolines, the alkines evi- 
dently form easily and are often so stable that 
is experienced in dehy- 
drating them to the stilbazoles. With these quina- 
zolone condensations, on the other hand, the al- 
kines either do not form at all or are so unstable 
that they immediately lose water and give the 
stilbazole. Neither hydrogen nor bromine can be 
added to the double bond of these stilbazoles, but 
bromine gives rise to substitution products. 
A large number of new aldehyde condensation 
products were prepared of the above types. Most 
of the styryl quinazolones are pale yellow and 
erystallize in fluffy masses of short silky needles. 
Often they show strong tribo-electrie properties. 
Those with a free hydrogen atom in position 3 
usually dissolve readily in solutions of the caustic 
alkalies and are reprecipitated by carbon dioxide. 
Incidentally, a number of new quinazolines were 
prepared by condensing various amino bodies with 
acylanthranils, and certain of them were tested 
with reference to their physiological effect upon 
animals. 
Under the conditions of ovr experiments, the 
group which reacted most readily with aldehydes 
was the 3-amino group, then the 2-methyl, then the 
7-amino, while the 2-amino refused to condense at 
all. Benzaldehyde proved much the easiest alde- 
hyde to condense with these groups, often reacting 
when all other aldehydes tried failed. 
M. T. Bogert, R. A. GoRTNER and A. H. KRoprFF: 
On Certain New Dyestuffs. 
By condensation of acylanthranils with aro- 
matic primary diamines, new amine bases result 
which can be used for the production of dyestuffs 
