We are working on Fisher Indole synthesis, but we are getting 15-20% impurity and some dimers also observed. During workup to purify these the yield will dropped upto 50 %
Problem is in the selectivity of your synthetic process. Try on use another way. Broad spectrum of examples: http://www.organic-chemistry.org/synthesis/heterocycles/indoles.shtm
References fro Wikipedia
Fischer, E.; Jourdan, F. (1883). "Ueber die Hydrazine der Brenztraubensäure". Berichte der Deutschen Chemischen Gesellschaft 16 (2): 2241–2245. doi:10.1002/cber.188301602141.
- Fischer, E.; Hess, O. (1884). "Synthese von Indolderivaten". Berichte der Deutschen Chemischen Gesellschaft 17 (1): 559–568. doi:10.1002/cber.188401701155.
- van Order, R. B.; Lindwall, H. G. (1942). "Indole". Chemical Reviews 30 (1): 69–96. doi:10.1021/cr60095a004.
- Robinson, B. (1963). "The Fischer Indole Synthesis". Chemical Reviews 63 (4): 373–401. doi:10.1021/cr60224a003.
- Robinson, B. (1969). "Studies on the Fischer indole synthesis". Chemical Reviews 69 (2): 227–250. doi:10.1021/cr60258a004.
- Allen, C. F. H.; Wilson, C. V. (1943). "The Use of N15 as a Tracer Element in Chemical Reactions. The Mechanism of the Fischer Indole Synthesis". Journal of the American Chemical Society 65 (4): 611–612. doi:10.1021/ja01244a033.
- Clusius, K.; Weisser, H. R. (1952). "Reaktionen mit 15N. III. Zum Mechanismus der Fischer'schen Indolsynthese". Helvetica Chimica Acta 35 (1): 400–406. doi:10.1002/hlca.19520350151.
- Wagaw, S.; Yang, B. H.; Buchwald, S. L. (1998). "A Palladium-Catalyzed Strategy for the Preparation of Indoles: A Novel Entry into the Fischer Indole Synthesis". Journal of the American Chemical Society 120 (26): 6621–6622. doi:10.1021/ja981045r.
Preform the phenyl hydrazone and run the reaction thermally in the absence of a lewis / bronsted catalyst in a microwave reactor.
It is difficult to give more advice without structural information.
For Fisher Indole synthesis to synthesize simple indole many methodes are available. If that is substituted indole, It is difficult to suggest without structural information
no methods are perfect for indole synthesis, chem is try, we must have more experiments.
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