# hydroxychloroquine (HCQ) Synthesis: Which mechanism?

Draw the product of the following reaction and provide an explanation for this reaction knowing that $$\mathrm{ROH}$$ or $$\mathrm{RNH_2}$$ + $$\mathrm{PhCl}$$ do not react at all.

I have no doubt that the answer is hydroxychloroquine (HCQ), but how would it be formed if the reaction: $$\mathrm{RNH_2}$$ + $$\mathrm{PhCl}$$ does not happen? Or, is the question hinting that the reaction takes the $$\mathrm{S_N1}$$ pathway where the phenylcation gets formed? If so, why does the Cl atom para to the nitrogen leave more readily than the other Chloride?