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

doi:10.1002/JHET.5570170306

Paper

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

Published Oct 21, 1980 · G. Ponticello, E. Engelhardt, M. B. Freedman

Journal of Heterocyclic Chemistry

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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.

Study Snapshot

This study presents a convenient method for synthesizing 2-chloro-5-hydroxynicotinonitrile (10) via 5-amino-2-chloro-3-methylpyridine (3), providing the basic metabolite 2 of (S)-2-(3-t-butylamino-2

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

An approach to peripheral vasodilator-beta-adrenergic blocking agents.

The syntheses of 2-phenyl- and 2-pyridyl-4-trifluoromethylimidazoles with 3-tert-butylamino-2-hydroxypropoxy moiety show potential as peripheral vasodilator-beta-adrenergic blocking agents with potential anti

Pyridine nucleosides related to 5-fluorouracil

This study demonstrates the successful synthesis of 5-fluoro-3-deazauridine, a related nucleoside to 5-fluorouracil, and its derivatives.

Citations

A carbon-13 Nmr assignment study of 3,5-diarylisoxazoles

Carbon-13 Nmr assignments of 3,5-diarylisoxazoles (I and II) in dimethylsulfoxide-d6 enable simultaneous production of both compounds using certain synthetic methods.