Process for the preparation of indoles

Details Process for the preparation of indoles Process for the preparation of indoles

1991-11-13

1993-01-12

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20904

Patent

active

051792117

ABSTRACT:
Indoles of the formula ##STR1## can be prepared by reaction of a phenylhydrazine of the formula ##STR2## which is unsubstituted in at least one ortho-position, with a ketone of the formula ##STR3## in an aqueous medium in the presence of an acid compound, less than 5 equivalents, based on 1 mol of phenylhydrazine, of an acid compound having a pK value of 1.3-4.5 being employed.

REFERENCES:
patent: 3639420 (1972-01-01), Illy et al.
patent: 4057530 (1977-11-01), Pigerol et al.
patent: 4062865 (1977-12-01), Moggi
CA 94:1748003 Fischer indole . . . 3-alkoxycarbonylindoles, Mills et al. p. 700, 1981.
CA 110:145047v Photochromic . . . derivatives. Iriyo et al. 1989 p. 675.
The Journal of Organic Chemistry, vol. 33, No. 11, Nov. 1968, pp. 4283-4285 Illy et al.
R. K. Brown in the Chemistry of Heterocyclic Compounds, vol. 25, Part one: Indoles, Chapter II, 1972, pp. 246-258.
Chemiken-Zeitung, 22 (1988), 37, Plancher, Synthesis . . . Indden.
J. Org. Chem., vol. 42, No. 14, 1977, pp. 2474-2480, Annelation of Pyridinium . . . Heterocycles, Chapman et al.
J. Am. Chem. Soc., 74 (1952), 3948 Fisher Indole Synthesis . . . Acid, Kissman et al.
Chemistry and Industry, Mar. 13, 1965, p. 473, Fischer Indole Synthesis and Ethylation of 2,3-Disubstituted Indoles with Polyphosphate Esters, by Y. Kanaoka et al.

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