Master Organic Chemistry Reaction Guide

Hofmann Rearrangement of Amides to Amines

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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Real-Life Example:

Org. Synth. 1950, 30, 3

DOI Link: 10.15227/orgsyn.030.0003

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Comment section

6 thoughts on “Hofmann Rearrangement of Amides to Amines

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

  2. 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.

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

  3. I’m wondering why the last example can react without amide. Is there something different happened? Or the carboxylic acid actually refers to amide?
    I would appreciate for your help.

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