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

proposed chloroquine synthesis

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Could you upload images of your desired synthesis please? –  CHM Jun 11 '12 at 15:56
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

3 Answers 3

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:

enter image description here

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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It's a pretty untypical approach to chloroquine and you didn't tell how you would synthesize 7-chloro-3-aminoquinoline and the secondary chloride ;-)

The classical synthesis of chloroquine is a bit different, using 4,7-dichloroquinoline, which is readily available from 3-chloroaniline, and 4-diethylamino-1-methylbutylamine.

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yes, it is quite possible as aromatic anines nitrogen being moore nucleophilic further the secondary chloro reacts easily, the reaction may either be SN1 or SN2. I have done couple of reaction of this type, if you need help feel free to contact me.

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Could you elaborate on how this reaction works, maybe with a breakdown of the mechanism? –  ManishEarth Jan 26 '13 at 8:44

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