Abstract
A solvent-free “one-pot” synthetic approach to 1-(3-iodopropyl)-4-methylquinolin-1-ium iodide is reported in the present work. The title compound is derived from N-alkylation of 4-methylquinoline with 1,3-diiodopropane proceeded at room temperature. The target quinolinium salt is obtained in a highly pure form. It’s structure was evaluated by 1H-NMR, 13C-NMR, and DEPT135 spectra.
Highlights
A solvent-free “one-pot” synthetic approach to 1-(3-iodopropyl)-4methylquinolin-1-ium iodide is reported in the present work
1-(3-iodopropyl)-4-methylquinolin-1-ium iodide is known as a key intermediate product for the synthesis of several commercially available dyes such as TOTO-1, YOYO-1, TOPRO-1, YOPRO-1 (Life Technologies), used as non-covalently binding fluorescent probes for nucleic acids [1–9]
Except from the formation of the title compound, this approach always yields a bis-N-quaternary side product [(1,1′-(propane-1,3-diyl)bis(4-methylquinoline1-ium)diiodide)], which is rarely mentioned in the literature
Summary
A solvent-free “one-pot” synthetic approach to 1-(3-iodopropyl)-4methylquinolin-1-ium iodide is reported in the present work. Classic methods for the synthesis of the quinolinium derivative, involve heating of the starting compounds in equimolar ratios using various solvents. Except from the formation of the title compound, this approach always yields a bis-N-quaternary side product [(1,1′-(propane-1,3-diyl)bis(4-methylquinoline1-ium)diiodide)], which is rarely mentioned in the literature.
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