TheGuy2000

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Howdy folks,
Hate to bring back some bad memories, but I'm struggling to find the mechanism which would get me from
N-benzylphthalimide + hydrazine ----ethanol--> to benzylamine and phthallhydrazide.
Thanks for any help. Does the hydrazine just attack the carbonyl here?
I'm pretty sure it's a Gabriel Synthesis.

Pax.
 

TheGuy2000

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bumpy, plz help me :confused: organic is making lose my mind...
 

Benjo

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what the hell are those compounds? Maybe give us an idea of what that nomenclature actually translates to in structure/functionality and we can help.
 

liverotcod

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My organic instructor waved the magic mechanism wand on Gabriel synthesis and said, "Don't worry about this one. Just know Fisher esterification." Here's a web page on Gabriel synthesis. It certainly looks like the hydrazine could do nucleophilic acyl substitution on the each of the carbonyls, releasing R-NH2 from first one side of the ring, then the other.
 
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