Destroyer Orgo #194

[prsndwg]

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Hi
this is the Q from 09 destroyer orgo #194.

what happens in the 2nd step?

I tried to draw it, but sorry if its small
Thanks in advance

 

[dfymarine]

looks like a Gabriel synthesis to me

check the mechanism: http://www.organic-chemistry.org/namedreactions/gabriel-synthesis.shtm

 

[joonkimdds]

very artistic~ 🙂
I think it's gabriel synthesis too.

 

[prsndwg]

i always thought NH2NH2 changes O of canbonyl into two H's!
Am I wrong?

 

[prsndwg]

bump

 

[namiie]

i always thought NH2NH2 changes O of canbonyl into two H's!
Am I wrong?

It is indeed a Gabriel synthesis. NH2NH2 is used for basic hydrazinolysis. After the SN2 reaction with the phthalimide and the halide, NH2NH2 is used to free up the amine.