I dont think fischer esterification will work. Better you have to protect amine and go with EDCI to activate acid and add your alcohol to get ester. Then you deprotect the amine.

if mention the exact molecule I can help you better

Hello, it depends also of the environment of your alcool and amine. Reactivity will be different if they are aromatic or aliphatic.

Well, if you use classic acid-catalyzed esterification procedure with strong acid, you probably could.

Thanks Sandeep Chandrashekharappa . Is it ok if I message you privately?

Because I wonder why I would need EDCI.

THanks Vladimir Khlebnikov , it is unlikely to work though, ain't it?

Maybe multiple products at best, no?

Ok you can message me

Joseph,

Classic esterification procedure almost always works if you substrate does not have acid-sensitive groups, if it is stable in strong acidic conditions, and when there are no specific issues with the isolation of your desired product after the reaction. It is not the best procedure for all the substrates though, that's why we have so many other conditions developed for this reaction.

I would like to give you more specific (and more useful answer), but unfortunately, it is not possible without knowing the structure of you starting material.

With all due respect,

Vladimir

Vladimir Khlebnikov

Thank you for your contribution, I'll message you privately if you don't mind.

Sure, you are welcome.