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

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

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.



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



Why do you use bromine to get amines?


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