Questions/Amines/While acidic or basi...
Preparation of AminesAmines

While acidic or basic hydrolysis can cleave N-alkylphthalimide to release the amine, what reagent is often preferred for milder cleavage, and what is the byproduct?

Expert Answer

Hydrazine ( NH2NH2NH_2NH_2 ) is often preferred (Ing-Manske procedure). It allows cleavage under milder conditions compared to harsh acid/base reflux. The byproduct is Phthalhydrazide, which is often an insoluble solid, facilitating easy separation of the desired soluble amine.

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