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Synthesis 1995; 1995(2): 147-149
DOI: 10.1055/s-1995-3886
short paper
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A Convenient, Short Synthesis of Desethylchloroquine [7-Chloro-4-(4’-ethylamino-1’-methyl-butylamino)quinoline]

Aslam M. Ansari, J. Cymerman Craig*
  • *Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco, California, 94143-0446, USA
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Publication Date:
31 December 2000 (online)

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A short, efficient 2-step synthesis of desethylchloroquine is achieved by generating an internal amide ion from the secondary nitrogen in chloroquine, followed by in situ reaction with 2,2,2-trichloroethyl chloroformate giving rapid elimination of ethylene. The carbamate thus produced easily undergoes deprotection to the target compound at room temperature.

desethylchloroquine - N-deethylation - elimination reaction - trichloroethyl chloroformate - internal amide ion