# Synthesis of Chloroquine from 7-Chloro-3-Amino quinoline

Can we get Chloroquine from 7-chloro-3-aminoquinoline by adding $\ce{CH3CHCl(CH2)3N(Et)2}$ ?

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Looking at the formulas for your two compounds, it seems like a simple substitution. What are you looking for in particular? –  F'x Jun 11 '12 at 22:17
I've added a drawing of the proposed synthesis with hydrogen chloride as the inferred elimination product. I flipped the pendant alkylamine to save space on the page. ChemFig rocks, btw. –  Richard Terrett Jun 12 '12 at 3:55

My intuition tells me that the nitrogen in the ring is more nucleophilic than the exocyclic amine. A quick-and-dirty electrostatic potential calculation using B88LYP/6-31G(d) on the PM3 geometry shows a large electron density (blue and violet) on the ring nitrogen and lower density (yellow) on the exocyclic amine:

Are there conditions that might work? Yes. Should you try it, if you need that molecule? Yes. Will it be difficult? Yes.

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