Ryan— On the Preparation of Amidoketones. 521 
Moreover, the time necessary for the several reactions, about 
eleven days, renders the method very tedious in practice. 
Second Method of Preparing Amidoketones.—By the well- 
known method of Gabriel’ for preparing primary amines, I have 
found that p-methyl-chlor-acetyl-benzene reacted with potassium 
phtalimide to give p-methyl-a-phtalimidoaceto-phenone. 
\ 
CH, - C,H,: CO: CH: NC OH, 
co 
which was hydrolysed with alcoholic potash to the corresponding 
phtalaminic acid :— 
CH; C,H, - CO CH : NH - CO: C,H, - COOH. 
On boiling the latter with concentrated hydrochloric acid 
under the reflux condenser, it returned partly to the original com- 
pound, and decomposed partly into phtallic acid and the 
hydrochloride of p-methyl-a-amidoacetophenone :— 
CH; : C,H, : CO: CH, : NH. - HCl. 
The yield of amidoketone was about 23 per cent. of the 
amount theoretically obtainable from the quantity of w-chloracety1! 
toluene used, and the time required for its preparation is less than 
two days. 
Thus, both for convenience, saving of time, and yield, the 
method of Gabriel is to be preferred for aromatic amidoketones. 
I].—ExprErimentTaL Part. 
A. First Method of Preparation.—Preparation of m-xylyl bro- 
mide OH; - C,H, - CH, Br. 
I 1 3 
The parent substance for the following experiments was pre- 
pared by the method of Radsziszewski and Wispek.’ 
310 gs. of bromine were allowed to drop slowly into 200 gs. of 
metaxylene heated to boiling in a glycerine bath. The hydro- 
bromic acid escaped by a long vertical tube which served to 
condense the xylene. The product, which was dark coloured, was 
* See Richter’s ‘‘ Organic Chemistry,”’ vol. i. 
2 Ber. (1882), 15, p. 1745. Ibid. (1885), 18, p. 1282. 
