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INDULINES

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Originally appearing in Volume V14, Page 507 of the 1911 Encyclopedia Britannica.
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INDULINES , a See also:

series of dyestuffs of See also:blue, bluish-red or See also:black shades, formed by the interaction of See also:para-amino See also:azo compounds with See also:primary monamines in the presence of a small quantity of a See also:mineral See also:acid. They were first discovered in 1863 (See also:English patent 3307) by J. See also:Dale and H. See also:Caro, and since then have been examined by many chemists (see O. N. Witt, Ber., 1884, 17, p. 74; O. See also:Fischer and E. Hepp, See also:Ann., 1890, 256, pp. 233 et seq.; F. Kehrmann, See also:Bet., 1891, 24, pp. 584, 2167 et seq.).

They are derivatives of the eurhodines (aminophenazines, aminonaphthophenazines), and by means of their diazo derivatives can be de-amidated, yielding in this way azonium salts; consequently they may be considered as amidated azonium salts. The first reaction giving a See also:

clue to their constitution was the See also:isolation of the intermediate azophenin by O. Witt (Jour. Chem. See also:Soc., 1883, 43, p. 115), which was proved by Fischer and Hepp to be dianilidoquinone dianil, a similar intermediate See also:compound being found shortly afterwards in the See also:naphthalene series. Azophenin, Ca,H24N4, is prepared by warming quinone dianil with See also:aniline; by melting together quinone, aniline and aniline hydrochloride; or by the See also:action of aniline on para-nitrosophenol or para-nitrosodiphenylamine. The indulines are prepared as mentioned above from aminoazo compounds: See also:NH2•C6H4N2•Celia-I-C6I-ISNH,-> HN : C6H3<N,CoH6> See also:C6H4, (aposafranine) or by condensing oxy- and amido-See also:quinones with phenylated ortho-diamines (F. Kehrmann, Ber., 1895, 28, p. 1714): H0>C6H2H+See also:C6H,NH>C6H4= 2H2O--HO>C6H2<N See also:C6H5 The indulines may be subdivided into the following See also:groups:—(I) benzindulines, derivatives of See also:phenazine; (2) isorosindulines; and (3) rosindulines, both derived from naphthophenazine; and (4) naphthindulines, derived from naphthazine. T NH:C6H3<N;.CaH6> C€See also:H4 NH: C€H3<N,CoH6>CioH6 I. Benzindulines.

II. Isorosindulines. NH: CioH5<N.CeHa>C€H4 NH: CioH5<NC6H6> CioHa The rosindulines and naphthindulines have a strongly basic See also:

character, and their salts possess a marked red See also:colour and See also:fluorescence. Benzinduline (aposafranine), C16H13N3, is a strong See also:base, but cannot be diazotized, unless it be dissolved in concentrated mineral acids. When warmed with aniline it yields anilido-aposafranine, which may also be obtained by the See also:direct oxidation of ortho-aminodiphenylamine. Isorosinduline is obtained from quinone dichlorimide and phenyl-13-naphthylamine; rosinduline from benzeneazo-a-naphthylamine and aniline and naphthinduline from benzeneazo-a-naphthylamine and naphthylamine.

End of Article: INDULINES

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