No abstract

The acid was then prepared by an alkaline hydrolysis of the ester, and crystallization from benzene-ligroin; m. p. 107-108°.3-(4'-Bromophenyl) -indanone VI.-To a solution of 7.9 g. of the above acid in 50 cc. of carbon disulfide was carefully added 5.2 g. of phosphorus pentachloride, and, after warming, all the solvent was removed by reducing the pressure. The residual oily chloride was taken up in 100 cc. of carbon disulfide, and, at 10-15°, 6.7 g. of anhydrous aluminum chloride was added. After stirring the mixture at room temperature for three hours and appropriate manipulation, 5 g. of the indanone, m. p. 59-60°, was secured, recrystallizing from benzene-petroleum ether.Oxidation.-To a boiling solution of 4 g. of the indanone in 30 cc. of acetic acid was added 4 g. of chromium trioxide; the 4'-bromo-2-benzoylbenzoic acid, m. p. 172-173°, was isolated in the usual way. A mixed melting point with an authentic sample* showed no depression.2-Bromo-3-(4 '-bromophenyl)-indanone X was secured in both stereoisomeric forms as described.1 The reduction to VI was carried out by adding the substance to an ethereal methylmagnesium iodide solution, refluxing for two hours, and appropriate manipulation. The indanone VI was readily isolated. Since one of the stereoisomers can be converted into the other, this fixes the structure of both forms of the dibromoindanones.

Table I Acbtylsulfanilamidoindazoles Acetylsulfanilamidoindazole M. p" °C. (uncor.