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ISATIN, C8H5NO2

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Originally appearing in Volume V14, Page 866 of the 1911 Encyclopedia Britannica.
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See also:

ISATIN, C8H5NO2 , in See also:chemistry, a derivative of indol, interesting on See also:account of its relation to See also:indigo; it may be regarded as the anhydride of ortho-aminobenzoylformic or isatinic See also:acid. It crystallizes in See also:orange red prisms which melt at 200-201° C. It may be prepared by oxidizing indigo with nitric or chromic acid (0. L. See also:Erdmann, Jour. prak. Chem., 1841, 24, p. 11); by boiling ortho-nitrophenylpropiolic acid with alkalis (A. See also:Baeyer, Ber., 188o, 13, p. 2259), or by oxidizing carbostyril with alkaline See also:potassium permanganate (P. Friedlander and H. Qstermaier, Ber., 1881, 14, p. 1921).

P. J. See also:

Meyer (See also:German Patent 26736 (1883)) obtains substituted isatins by condensing See also:para-toluidine with dichloracetic acid, oxidizing the product with See also:air and then hydrolysing the oxidized product with hydrochloric acid. T. Sandmeyer (German See also:Patents 113981 and 119831 (1899)) obtained isatin-a-anilide by condensing See also:aniline with See also:chloral See also:hydrate and See also:hydroxylamine, an intermediate product isonitrosodiphenylacetamidine being obtained, which is converted into isatin-aanilide by sulphuric acid. This can be converted into indigo II by reduction with ammonium sulphide. Isatin dissolved in concentrated sulphuric acid gives a See also:blue coloration with thiophene, due to the formation of indophenin (see Abst. J.C.S., 1907). Concentrated nitric acid oxidizes it to oxalic acid, and See also:alkali See also:fusion yields aniline. It dissolves in soda forming a See also:violet See also:solution, which soon becomes yellow, a See also:change due to the transformation of See also:sodium N-isatin into sodium isatate, the aciisatin See also:salt being probably formed intermediately (See also:Heller, Abst. J.C.S., 1907, i. p. 442).

Most metallic salts are N-derivatives yielding N-methyl See also:

ethers; the See also:silver salt is, however, an 0-derivative, yielding an 0-methyl See also:ether (A. v. Baeyer, 1883; W. See also:Peters, Abst. J.C.S., 1907, i. p. 239).

End of Article: ISATIN, C8H5NO2

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