Synthesis of 2-chloro-5-hydroxynicotinonitrile: The required intermediate in the total synthesis of a hydroxylated metabolite of (S)-2-(3-t-butylamino-2-hydroxypropoxy)-3-cyanopyridine
1
Merck Sharp & Dohme Research Laboratories, West Point, Pennsylvania 19486.
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Publication type: Journal Article
Publication date: 1980-05-01
scimago Q3
wos Q2
SJR: 0.362
CiteScore: 4.7
Impact factor: 2.4
ISSN: 0022152X, 19435193
Organic Chemistry
Abstract
A convenient method for the synthesis of 2-chloro-5-hydroxynicotinonitrile (10) via 5-amino-2-chloro-3-methylpyridine (3) is described. Subsequent conversions provided the basic metabolite 2 of (S)-2-(3-t-butylamino-2-hydroxypropoxy)-3-cyanopyridine (1). 13C Nmr data is also presented to characterize 2-chloro-5-fluoro-3-methylpyridine (5), a by-product in the Schiemann reaction having unexpected 1H and 19F nmr spectra.
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Ponticello G. S. et al. Synthesis of 2-chloro-5-hydroxynicotinonitrile: The required intermediate in the total synthesis of a hydroxylated metabolite of (S)-2-(3-t-butylamino-2-hydroxypropoxy)-3-cyanopyridine // Journal of Heterocyclic Chemistry. 1980. Vol. 17. No. 3. pp. 445-448.
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Ponticello G. S., Engelhardt E. L., Freedman M. B., Baldwin J. J. Synthesis of 2-chloro-5-hydroxynicotinonitrile: The required intermediate in the total synthesis of a hydroxylated metabolite of (S)-2-(3-t-butylamino-2-hydroxypropoxy)-3-cyanopyridine // Journal of Heterocyclic Chemistry. 1980. Vol. 17. No. 3. pp. 445-448.
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TY - JOUR
DO - 10.1002/jhet.5570170306
UR - https://doi.org/10.1002/jhet.5570170306
TI - Synthesis of 2-chloro-5-hydroxynicotinonitrile: The required intermediate in the total synthesis of a hydroxylated metabolite of (S)-2-(3-t-butylamino-2-hydroxypropoxy)-3-cyanopyridine
T2 - Journal of Heterocyclic Chemistry
AU - Ponticello, Gerald S
AU - Engelhardt, Edward L
AU - Freedman, Mark B
AU - Baldwin, John J
PY - 1980
DA - 1980/05/01
PB - Wiley
SP - 445-448
IS - 3
VL - 17
SN - 0022-152X
SN - 1943-5193
ER -
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@article{1980_Ponticello,
author = {Gerald S Ponticello and Edward L Engelhardt and Mark B Freedman and John J Baldwin},
title = {Synthesis of 2-chloro-5-hydroxynicotinonitrile: The required intermediate in the total synthesis of a hydroxylated metabolite of (S)-2-(3-t-butylamino-2-hydroxypropoxy)-3-cyanopyridine},
journal = {Journal of Heterocyclic Chemistry},
year = {1980},
volume = {17},
publisher = {Wiley},
month = {may},
url = {https://doi.org/10.1002/jhet.5570170306},
number = {3},
pages = {445--448},
doi = {10.1002/jhet.5570170306}
}
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MLA
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Ponticello, Gerald S., et al. “Synthesis of 2-chloro-5-hydroxynicotinonitrile: The required intermediate in the total synthesis of a hydroxylated metabolite of (S)-2-(3-t-butylamino-2-hydroxypropoxy)-3-cyanopyridine.” Journal of Heterocyclic Chemistry, vol. 17, no. 3, May. 1980, pp. 445-448. https://doi.org/10.1002/jhet.5570170306.