Effect of dimethyl sulfoxide and dimethylformamide on the stability of 4-halo-8quinolinols / Herman Gershon, Donald D. Clarke, and John J. McMahon Department of Chemistry, Fordham University, Bronx, NY 10458-9993, USA New York Botanical Garden, Bronx, NY 10458-9993, USA

Authors

Herman Gershon, New York Botanical Garden. Harding Laboratory
Donald Dudley Clarke PhD, Fordham UniversityFollow
John J. McMahon, Fordham University

Document Type

Article

Keywords

Degradation of 4-halo-8-quinolinols in DMSO and DMF, 4-Halo-8-quinolinols stable in pyridine-d5, 5-Chloro-4,8-quinolindiol, 5-Bromo-4,8-quinolindiol, 3,5-Dibromo-4,8-quinolindiol

Disciplines

Biochemistry

Abstract

Polyhalo-8-quinolinols with chlorine or bromine in position 4 were not stable in DMSO or DMF. The degradation product from 4,5-dichloro-8-quinolinol was 5-chloro-4,8-quinolindiol and the major product from 4,5-dibromo-8-quinolinol was 3,5-dibromo-4,8-quinolindiol. 4,5,7-Trichloro- and 4,5,7-tribromo-8-quinolinols yielded similar hydrolytic products, and for the bromo compound, a rebrominated product in DMSO. In DMF rebrornination did not occur. In pyridine-d5 these reactions did not take place, indicating a special ability of DMSO and DMF to cause such hydrolysis at position 4 of 4-halo-8-quinolinols

Article Number

1049

Publication Date

2003

Recommended Citation

Gershon, Herman; Clarke, Donald Dudley PhD; and McMahon, John J., "Effect of dimethyl sulfoxide and dimethylformamide on the stability of 4-halo-8quinolinols / Herman Gershon, Donald D. Clarke, and John J. McMahon Department of Chemistry, Fordham University, Bronx, NY 10458-9993, USA New York Botanical Garden, Bronx, NY 10458-9993, USA" (2003). Chemistry Faculty Publications. 50.
https://research.library.fordham.edu/chem_facultypubs/50

Comments

Monatshefte für chemie 134:1099-1104. http://dx.doi.org/10.1007/s00706-003-0026-0