SYNTHESIS OF THE ENANTIOMERS OF LORO-4-QUINOLINYL)AMINO]PENTYL]ETHYLAMINO]ETHANOL, [3-H-3]-HYDROXYCHLOUOQUINE

The enantiomers of loro-1-quinolinyl)amino]pentyl]ethylamino]ethanol, [3-H-3]-hydroxychloroquine, (R)-8 and (S)-8, have been prepared in two steps from the known precursors 4,7-dichloro-3-iodoquinoline, 4, and the enantiomers of 2-[(4-aminopentyl)ethylamino]ethanol, (R)-2 and (S) -2, by formation of the enantiomers of iodo-4-quinolinyl)amino]pentyl] ethylamino]ethanol, (R)-3 and (S)-3, and subsequent reductive deiodina tion with tritium gas over 10% palladium on charcoal.