Abstract
Bromination of 2-methyl-3-phenyl-5-nitroindoles has given previously unknown 2-bromoethyl-3-phenyl-5-nitroindoles, which were converted by the Delepine reaction into 2-aminomethyl-3-phenyl-5-nitroindoles. One of these (1-methyl-2-aminomethyl-3-phenyl-5-nitroindole) was also obtained by reductive amination of 1-methyl-2-formyl-3-phenyl-5-nitroindole by the Leuckart-Wallach reaction.
Similar content being viewed by others
Literature cited
M. D. Mashkovskii, Drugs [in Russian], Meditsina, Moscow (1977), Vol. 1, p. 34.
S. Sakai, S. Kitagava, and H. Yamamoto, Arzneim. Forsch.,22, 534 (1972).
S. Inaba, K. Ishizumi, K. Mori, and H. Yamamoto, Chem. Pharm. Bull.,19, 722 (1971).
H. Yamamoto, S. Inaba, T. Hirohashi, T. Okamoto, K. Ishizumi, M. Yamamoto, I. Maruyama, K. Mori, and T. Kobayashi, Patent No. 1,811,830 (BRD); Chem. Abstr.75, 129844 (1971).
H. Yamamoto, S. Inaba, T. Hirohachi, T. Okamoto, K. Ishizumi, M. Yamamoto, I. Maruyama, K. Morik, and T. Kobayashi, Patent No. 1,817,761 (BRD); Chem. Abstr.,74, 3671 (1971).
H. Yamamoto, S. Inaba, T. Okamoto, T. Hirohashi, K. Ishizumi, M. Yamamoto, I. Maruyama, K. Mori, and T. Kobayashi, Patent No. 1,806,106 (BRD); Chem. Abstr.,71, 70659 (1969).
M. Yamamoto, S. Inaba, T. Hirohashi, K. Ishiguro, I. Maruyama, and K. Morik, Jap. Patent No. 7,102,016; Chem. Abstr.,74, 87826 (1971).
C. M. Atkinson, J. C. E. Simpson, and A. Taylor, J. Chem. Soc.,1, 165 (1954).
A. R. Frasca, An. Asoc. Quim. Arg.,50, 162 (1962).
É. S. Krichevskii, V. I. Shvedov, L. B. Altukhova, and A. N. Grinev, Inventor's Certificate No. 548028 (USSR); Byull. Izobret., No. 37, 268 (1982).
É. S. Krichevskii, V. I. Shvedov, L. B. Altukhova, and A. N. Grinev, Inventor's Certificate No. 540,457 (USSR); Byull. Izobret., No. 37, 269 (1982).
F. Millich and E. I. Becker, J. Org. Chem.,23, 1096 (1958).
É. S. Krichevskii, V. I. Shvedov, L. B. Altukhova, and A. N. Grinev, Inventor's Certificate No. 590,948 (USSR); Byull. Izobret., No. 37, 268 (1982).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1648–1651, December, 1983.
Rights and permissions
About this article
Cite this article
Krichevskii, É.S., Romanova, O.B. & Grinev, A.N. A new approach to the synthesis of 2-aminomethyl-3-phenyl-5-nitroindole. Chem Heterocycl Compd 19, 1302–1305 (1983). https://doi.org/10.1007/BF00842836
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00842836