1,3-Xylyl-5-bromo-4-nitrile, CeH2(CH3)2BrCN.-The bromoxylidine was converted into the nitrile by the .Gattermann-Sandmeyer reaction. In the distillation with steam the nitrile crystallized in the condenser, from which it was removed with hot alcohol. It crystallized in needles which melted at 86-87°. A by-product appeared in the receiver. It boiled at 205°and was therefore regarded as 5-bromo-1,3-dimethylbenzene.Anal. Caled, for CsHgBrN: Br, 38.05. Found: 38.00.1 -(5-Bromo-1,3-xyly 1-4-azo)-2-naphthol, C6H2(CHa)2BrN2Ci2H6OH.-The bromoxylidine was diazotized and coupled with 2-naphthol in the presence of sodium hydroxide. The crude red precipitate melted at 132°. Recrystallization from a mixture of alcohol and petroleum ether gave rich red needles melting at 136 °.Anal. Caled, for CisHi5ON2Br: Br, 23.50. Found: 23.15.l-(5-Bromo-l,3 -xyly 1-4-azo) -4-phenol, C6H2 (CHa)2BrN 2C6H4OH .-On coupling phenol with diazotized bromoxylidine a dark yellow precipitate formed, weight 3 g. from 2 g. of the xylidine. It was recrystallized from 90% acetic acid, or from a mixture of 3 parts of benzene and 7 parts of alcohol, to give small orange-colored crystals which melt at 166°.

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Fraction 2 was analyzed with the following results.

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