Effect of N-halosucinimides on 5-, 7- and 5,7-8-quinolinol sulfonic acids / Herman Gershon, Muriel Gershon, and Donald D. Clark Harding Laboratory, the New York Botanical Garde, Fordham University, Bronx, New York 10458, USA

Authors

Herman Gershon, New York Botanical Garden. Harding Laboratory
Muriel Gershon, New York Botanical Garden. Harding Laboratory
Donald Dudley Clarke PhD, Fordham UniversityFollow

Document Type

Article

Keywords

5-iodo-8-quinolinol, 7-iodo-8- quinolinol, 5-, 7- and 5, 7-8-quinolinolsulfonic acids, reaction with NXS

Disciplines

Biochemistry

Abstract

8-Quinolinol 5-, 7- and 5,7-sulfonic acids were treated with N-halosuccinimides (NXS) where the halogen atom was chlorine, bromine or iodine under different conditions of solvent, temperature and time. Under neutral or basic conditions the sulfonic acid group was retained while in dilute acid the S03H group was largely displaced by halogen. Excess NXS caused additional electrophilic substitution. Mild hydrolysis of 5-iodo-8-quinolinol- 7-sulfonic acid and 7-iodo-8-quinolinol-5-sulfonic acid with 15% sulfuric acid in acetic acid formed the 5- and 7-iodo-8-quinolinol respectively in high yield

Article Number

1007

Publication Date

2007

Recommended Citation

Gershon, Herman; Gershon, Muriel; and Clarke, Donald Dudley PhD, "Effect of N-halosucinimides on 5-, 7- and 5,7-8-quinolinol sulfonic acids / Herman Gershon, Muriel Gershon, and Donald D. Clark Harding Laboratory, the New York Botanical Garde, Fordham University, Bronx, New York 10458, USA" (2007). Chemistry Faculty Publications. 8.
https://research.library.fordham.edu/chem_facultypubs/8

Comments

Trends in heterocyclic chemistry. 12:67-73