Naoh cl2 h2o in forming amines

[akimhaneul]

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There is a reaction on organic odyssey that goes from benzamide to aniline using NaOH Cl2 H2O. How does this work? Is NaOH used for reduction?

 

[DentalAptitude]

Can you post a picture? This reaction wouldn't be possible as far as i'm aware, given the fact that a methylene group (CH2) would have to be displaced!


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[acemason]

I believe this is actually the Hoffman Rearrangement reaction. It can actually be done with Cl2 instead of Br2 like we are used to seeing. Chad covered it in his OC videos in section 4.4. For the Hoffmann Rearrangement, we just need a strong base, halogen, water, and heat. The entire C=O is lost.