I run a reaction of 4-aminobenzoic acid and 1-naphthoeyl chloride to make amide bond. Et3N is added to neutralize the CL which produced from 1-naphthoeyl chloride as a result of amide bond formation. the salt formation of Et3N HCL is suspected. I think my product will be partial soluble in water.
Your product seems to be insoluble in water when it is protonated. Dissolve your product in slightly basic conditions then add HCl to reach pH < 2-3 and your product will precipitate then filter it. The unreacted PBA is also eliminated.
you mean to esterify acyl chloride first then reacted with amine, is so what are the conditions needed ?
You may want to check also the following related discussion: https://www.researchgate.net/post/Removal_of_Et3NHCl_from_a_moisture_sensitive_compound
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