Synthesis of the enantiomers of [3‐3H]‐2‐[[4‐[(7‐chloro‐4‐quinolinyl)‐amino]pentyl]ethylamino]ethanol, [3‐3H]‐hydroxychloroquine

The enantiomers of [3-3H]-2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]ethanol,[3-3H]-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 2-[[4-[(7-chloro-3-iodo-4-quinolinyl)amino]pentyl]ethylamino]ethanol, (R)-3 and (S)-3, and subsequent reductive deiodination with tritium gas over 10% palladium on charcoal.