Hofmann Rearrangement of Amides to Amines

by James

Description: When amides are treated with chlorine and base, a rearrangement occurs, resulting in the loss of carbon dioxide and the formation of an amine.
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{ 4 comments… read them below or add one }

Lauren Benning December 9, 2012 at 11:48 pm

How do the last two reactions in your examples work if there is no amide to start with? Where does the nitrogen come from?


Andrew Ross April 8, 2013 at 1:50 am

Would you be willing to post an example where Pyruvic acid (2-oxopropanoic acid) and N-hydroxymethanamine react under acidic conditions (H3O+) to form Peptin (N-methylacetamide)? The electron flow of this reaction is quite confusing.


james April 10, 2013 at 9:55 pm

Ah the Beckmann rearrangement. Very closely related! I should put it up here, but in the meantime… there’s always Wikipedia


Sheriff September 28, 2013 at 4:52 pm

Why do you use bromine to get amines?


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