304 PROCEEDINGS OF THE AMERICAN ACADEMY 



a felt of small white needles, often arranged in fagots or groups like 

 an hour-glass ; it is not very stable, changing to a dirty pink on ex- 

 posure to the air, even when dry. The substance analyzed melted at 

 212° with a good deal of blackening, but we do not place much reli- 

 ance on this melting point, as the sample used was a good deal colored. 

 It is almost insoluble in cold, soluble in hot water ; soluble in hot 

 alcohol ; insoluble or nearly so in ether or chloroform ; not freely 

 soluble in benzol or carbonic disulphide, even when hot ; freely soluble 

 in hot glacial acetic acid. Sodic hydrate dissolves it, giving a pinkish 

 or pale magenta solution ; ammonic hydrate at first seems to have no 

 action, but on standing the liquid and solid turn dark bluish green ; 

 potassic carbonate in aqueous solution does not dissolve it. It seems 

 therefore to have the properties of a phenol. Neither picric acid in 

 henzol solution, nor ferric chloride with an alcoholic solution of the 

 base, produced any change of color. If some of the free base was 

 boiled with dilute sulphuric acid and a piece of pine, the wood was 

 turned a dull orange-red. 



As to the constitution of this base, it has been determined by work* 

 done in this laboratory on the bromdinitrophenylmalonic ester that 

 the nitro group, from which the amido group is formed, is in the para 

 position to the carbon side chain. The bromine is probably in the 

 ortho position, since all our work with the tetrabromdinitrobenzol has 

 shown that only three of its atoms of bromine can be replaced easily ; 

 and, as the compounds made from this substance are so closely analo- 

 gous to those prepared from the tribromdinitrobenzol, it is fair to 

 infer that the three symmetrical (meta) atoms of bromine are those 

 which can be removed, and that the fourth more stable atom of 

 bromine is the one in the unsymmetrical (ortho) position ; the atom 

 of bromine, therefore, which reduction takes away from the dibrom- 

 dinitrophenylmalonic ester, would be that in the meta position, and 

 the base would be accordingly orthobromparamidooxindol. 



Properties of the Chloride of Bromamidooxindol, 

 C G H 2 BrNH 2 (CH 2 CONH)HClH 2 0. 



When crystallized from water, the substance forms needles, or 

 prisms, sometimes as much as a centimeter long and a millimeter 

 thick, which seem to belong to the monoclinic system, and usually 

 have a yellowish color; we think, however, that this color is due to 

 partial oxidation, and that the substance is white when pure. When 



* These Proceedings, xxiv. 249, 250. 



