ACRIDINE, C13H9N

This article appears in Volume V01, Page 155 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: A10-ADA

ACRIDINE, C13H9N , in

chemistry

, a heterocyclic ring compound found in crude coal-tar anthracene. It may be separated by shaking out with dilute sulphuric acid, and then precipitating the sulphuric acid solution with potassium bichromate, the resulting acridine bichromate being decomposed by ammonia. It was first isolated in 1890 by C. Graebe and H.

Caro

CARO, ANNIBALE (1507-1566)
CARO, ELME MARIE (1826-1887)

(Ann., 1871, 158, p. 265). Many synthetic processes are known for the production of acridine and its derivatives. A. Bernthsen (Ann., 1884, 224, p. 1) condensed diphenylamine with fatty acids, in the presence of zinc chloride. Formic acid yields acridine, and the higher homologues give derivatives substituted at the meso carbon atom,
N N +H000HC6H5 /INC6H5-C6H4CI> C6H4
C6H6NHC6H6 CHO CH
N N
L +CH3000H- C6H5/I\C6H5- C6H4C6H4 OCH, C(CH3) Acridine may also be obtained by passing the vapour of phenyl-
ortho-toluidine through a red-hot tube (C. Graebe, Bee., 1884, 17, p. 1370); by condensing diphenylamine with chloroform, in presence of
aluminium

See Also:
ALUMINIUM (symbol Al; atomic weight 27.0)
chloride (0. Fischer, Ber., 1884, 17, p. 102) ; by passing the vapours of orthoaminodiphenylmethane over heated litharge (O. Fischer); by
heating

See Also:
HEATING
salicylic aldehyde with aniline and zinc chloride to 26o C. (R. Mohlau, Bee., r886, 19, p. 2452); and by distilling acridone over zinc dust (C. Graebe, Ber., 1892, 25, p. 1735).
Acridine and its homologues are very
stable

See Also:
STABLE
compounds of feebly basic character. They combine readily with the alkyl iodides to form alkyl acridinium iodides, which are readily trans-formed by the action of alkaline potassium ferricyanide to N-alkyl acridones. Acridine crystallizes in needles which melt at 11o C. It is characterized by its irritating action on the skin, and by the blue fluorescence shown by solutions of its salts. On oxidation with potassium permanganate it yields acridinic acid (
quinoline

See Also:
QUINOLINE (Benzopyridine), C9H7N
-a-3-dicarboxylic acid) C9H5N(000H)2. Numerous derivatives of acridine are known and may be prepared by methods analogous to those used for the formation of the parent base. For the preparation of the naphthacridines, see F.
Ullmann

See Also:
ULLMANN, KARL (1796-1865)
, German Patents 117472, 118439, 127.586, 128754, and also Ber., 1902, 35, pp. 316, 2670. Phenyl-acridine is the parent base of chrysaniline, which is the
chief

See Also:
CHIEF (from Fr. chef, head, Lat. caput)
constituent of the dye-stuff phosphine (a bye-product in the manufacture of rosaniline). Chrysaniline (diamino-phenylacridine) forms red-coloured salts,which dye
silk

See Also:
SILK
and wool a fine yellow; and the solutions of the salts are characterized by their fine yellowish-green fluorescence. It was synthesized by 0. Fischer and G. Koerner (Ber., 1884, 17, p. 203) by condensing ortho-nitrobenzaldehyde with aniline, the resulting ortho-nitro-para-diamino-triphenylmethane being reduced to the corresponding orthoamino compound, which on oxidation yields chrysaniline. Benzoflavin, an isomer of chrysaniline, is also a dye-stuff, and has been prepared by K. Oehler (English Patent 9614) from meta-phenylenediamine and benzaldehyde. These substances condense to form tetra-aminotriphenylmethane, which, on
heating

See Also:
HEATING
with acids, loses ammonia and yields diaminodihydrophenylacridine, from which benzoflavin is obtained by oxidation. It is a yellow powder, soluble in hot water. The formulae of these substances are:
/N/ N\I INH. H2NI \I/N I/ INH2
/Nc /\/ \/\0/ \/ /\I
N H2
Chrysaniline. Benzoflavin.

End of Article: ACRIDINE, C13H9N

If you wish, you can link directly to this article.

<a href="http://jcsm.org/StudyCenter/Encyclopedia/A10_ADA/ACRIDINE_C13H9N.html"> ACRIDINE, C13H9N </a>

(Previous)
ACRE, or AQUIRY

(Next)
ACRO (or ACRON), HELENIUS

JCSM was founded in 1997 and exists to help the community and bring people into a life-changing and productive relationship with Jesus Christ. JCSM offers over 200,000 free web pages, including its weekly inspirational emails that were sent continuously for over a decade.

Jesus Christ Saves Ministries
P.O. Box 9297
San Diego, CA 92169
1-888-887-0417 or Email