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Encyclopedia Britannica



ISATIN, C8H5NO2

This article appears in Volume V14, Page 866 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: INV-JED
ISATIN, C8H5NO2 , in
chemistry
 , a derivative of indol, interesting on account of its relation to indigo; it may be regarded as the anhydride of ortho-aminobenzoylformic or isatinic acid. It crystallizes in orange red prisms which melt at 200-201 C. It may be prepared by oxidizing indigo with nitric or chromic acid (0. L. Erdmann, Jour. prak. Chem., 1841, 24, p. 11); by boiling ortho-nitrophenylpropiolic acid with alkalis (A. Baeyer, Ber., 188o, 13, p. 2259), or by oxidizing carbostyril with alkaline potassium permanganate (P. Friedlander and H. Qstermaier, Ber., 1881, 14, p. 1921). P. J. Meyer (German Patent 26736 (1883)) obtains substituted isatins by condensing para-toluidine with dichloracetic acid, oxidizing the product with air and then hydrolysing the oxidized product with hydrochloric acid. T. Sandmeyer (German Patents 113981 and 119831 (1899)) obtained
isatin
 -a-anilide by condensing aniline with chloral hydrate and
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 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
alkali
  fusion yields aniline. It dissolves in soda forming a
violet
  solution, which soon becomes yellow, a
change
  due to the transformation of sodium N-isatin into sodium isatate, the aciisatin
salt
  being probably formed intermediately (
Heller
 , Abst. J.C.S., 1907, i. p. 442). Most metallic salts are N-derivatives yielding N-methyl
ethers
 ; the silver
salt
  is, however, an 0-derivative, yielding an 0-methyl ether (A. v. Baeyer, 1883; W. Peters, Abst. J.C.S., 1907, i. p. 239).
c(co
N >
co co Cton)
NRa.t Iowa*


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