Copyright (c) 2015 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Preparation and Characterization of Primary Amines by Potassium Borohydride-Copper Chloride System from Nitriles
Corresponding Author(s) : Xinliang Xu
Asian Journal of Chemistry,
Vol. 27 No. 10 (2015): Vol 27 Issue 10
Abstract
Nitriles undergo reduction to primary amines under optimized conditions at 50 °C using 0.25 equiv of copper chloride and 3.0 equiv of potassium borohydride in 80 % isopropanol. The aromatic and aralkyl nitriles could be effectively reduced in yield ranging from 60 to 90 %.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- J.Z. Saavedra, A. Resendez, A. Rovira, S. Eagon, D. Haddenham and B. Singaram, J. Org. Chem., 77, 221 (2012); doi:10.1021/jo201809a.
- D. Haddenham, L. Pasumansky, J. DeSoto, S. Eagon and B. Singaram, J. Org. Chem., 74, 1964 (2009); doi:10.1021/jo8023329.
- (a) J.C. Robinson and J.H.R. Snydr, Org. Synth., 3, 720 (1946); (b) G.J. Roth and P. Lustenberger, US Patent 20050245500 (2005); (c) K. Kayser, M.P. Glenn, S.M. Sebti, J.Q. Cheng and A.D. Hamilton, Bioorg. Med. Chem. Lett., 17, 2068 (2007); doi:10.1016/j.bmcl.2007.01.004.
- K. Suda, F. Hino and C. Yijima, J. Org. Chem., 51, 4232 (1986); doi:10.1021/jo00372a024.
- M. Periasamy and M. Thirumalaikumar, J. Organomet. Chem., 609, 137 (2000); doi:10.1016/S0022-328X(00)00210-2.
- S. Itsuno, Y. Sakurai and K. Ito, Synthesis, 995 (1988); doi:10.1055/s-1988-27782.
- (a) T. Satoh, S. Suzuki, Y. Suzuki, Y. Miyaji and Z. Imai, Tetrahedron Lett., 10, 4555 (1969); doi:10.1016/S0040-4039(01)88749-9; (b) S. Caddick, A.K. de K. Haynes, D.B. Judd and M.R.V. Williams, Tetrahedron Lett., 41, 3513 (2000); doi:10.1016/S0040-4039(00)00410-X; (c) S.W. Heinzman and B. Ganem, J. Am. Chem. Soc., 104, 6801 (1982); doi:10.1021/ja00388a063.
- S. Yoo and S.H. Lee, Synlett, 1990, 419 (1990); doi:10.1055/s-1990-21113.
- A.S.B. Prasad, J.V.B. Kanth and M. Periasamy, Tetrahedron, 48, 4623 (1992); doi:10.1016/S0040-4020(01)81236-9.
- M.B. Smith and J. March, March’s Advanced Organic Chemistry, p. 577 (2009).
References
J.Z. Saavedra, A. Resendez, A. Rovira, S. Eagon, D. Haddenham and B. Singaram, J. Org. Chem., 77, 221 (2012); doi:10.1021/jo201809a.
D. Haddenham, L. Pasumansky, J. DeSoto, S. Eagon and B. Singaram, J. Org. Chem., 74, 1964 (2009); doi:10.1021/jo8023329.
(a) J.C. Robinson and J.H.R. Snydr, Org. Synth., 3, 720 (1946); (b) G.J. Roth and P. Lustenberger, US Patent 20050245500 (2005); (c) K. Kayser, M.P. Glenn, S.M. Sebti, J.Q. Cheng and A.D. Hamilton, Bioorg. Med. Chem. Lett., 17, 2068 (2007); doi:10.1016/j.bmcl.2007.01.004.
K. Suda, F. Hino and C. Yijima, J. Org. Chem., 51, 4232 (1986); doi:10.1021/jo00372a024.
M. Periasamy and M. Thirumalaikumar, J. Organomet. Chem., 609, 137 (2000); doi:10.1016/S0022-328X(00)00210-2.
S. Itsuno, Y. Sakurai and K. Ito, Synthesis, 995 (1988); doi:10.1055/s-1988-27782.
(a) T. Satoh, S. Suzuki, Y. Suzuki, Y. Miyaji and Z. Imai, Tetrahedron Lett., 10, 4555 (1969); doi:10.1016/S0040-4039(01)88749-9; (b) S. Caddick, A.K. de K. Haynes, D.B. Judd and M.R.V. Williams, Tetrahedron Lett., 41, 3513 (2000); doi:10.1016/S0040-4039(00)00410-X; (c) S.W. Heinzman and B. Ganem, J. Am. Chem. Soc., 104, 6801 (1982); doi:10.1021/ja00388a063.
S. Yoo and S.H. Lee, Synlett, 1990, 419 (1990); doi:10.1055/s-1990-21113.
A.S.B. Prasad, J.V.B. Kanth and M. Periasamy, Tetrahedron, 48, 4623 (1992); doi:10.1016/S0040-4020(01)81236-9.
M.B. Smith and J. March, March’s Advanced Organic Chemistry, p. 577 (2009).