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Synthesis of 2-Amino-5-hydroxypyridine via Demethoxylation
Corresponding Author(s) : J. Cheng
Asian Journal of Chemistry,
Vol. 28 No. 6 (2016): Vol 28 Issue 6
Abstract
A convenient and efficient four-step synthesis of 2-amino-5-hydroxypyridine can be achieved by protective reaction of 2-amino-5-bromopyridine in the presence of 2,5-hexanedione to yield 5-bromo-2-(2,5-dimethyl-1H-pyrrol-1yl)pyridine, methoxylation with sodium methylate to give 5-methoxy-2-(2,5-dimethyl-1H-pyrrol-1yl)pyridine, deprotective reaction with hydroxylamine hydrochloride to produce 2-amino-5-methoxypyridine and demethylation with 95 % H2SO4 to afford the title compound in an overall yield of 45 %.
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- D.L. Flynn, T.M. Caldwell, T. Samarakoon, L. Vogeti, M.D. Kaufman, W.C. Patt and Y. Ahn, US Patent 275016 (2014).
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- H.L. Yale and J.T. Sheehan, US Patent 4022897 (1977).
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- G.H. Ladouceur, R.D. Connell, A. Campbell, T.G. Lease, J.H. Cook and J. Baryza, EP Patent 1054881 (2008)
References
D.L. Flynn, T.M. Caldwell, T. Samarakoon, L. Vogeti, M.D. Kaufman, W.C. Patt and Y. Ahn, US Patent 275016 (2014).
M.A. Khanfar, L. Quinti, H. Wang, S.H. Choi, A.G. Kazantsev and R.B. Silverman, Eur. J. Med. Chem., 76, 414 (2014); doi:10.1016/j.ejmech.2014.02.003.
T.D. Aicher, J.R. Bencsik, S.A. Boyd, K.R. Condroski, J.B. Fell, J.P. Fisher, R.J. Hinklin, S.A. Pratt, A. Singh and T.M. Turner, WO Patent 146335 (2011).
S. Ahmad, K. Ngu and W.N. Washburn, US Patent 0093508 (2007).
B.R.R. Kesteleyn and W.B.G. Schepens, WO Patent 113290 (2007).
J.A. Moore and F.J. Marascia, J. Am. Chem. Soc., 81, 6049 (1959); doi:10.1021/ja01531a047.
H.L. Yale and J.T. Sheehan, US Patent 4022897 (1977).
C. Scudi, J. Biochem., 218, 587 (1956).
A. Lützen, M. Hapke, H. Staats and J. Bunzen, Eur. J. Org. Chem., 20, 3948 (2003); doi:10.1002/ejoc.200300192.
G.H. Ladouceur, R.D. Connell, A. Campbell, T.G. Lease, J.H. Cook and J. Baryza, EP Patent 1054881 (2008)