Schmidt reaction

Also known as: Schmidt rearrangement

Schematic of the Schmidt reaction. Reagents: hydrazoic acid (HN3), acid catalyst, aldehyde, ketone, carboxylic acid, tertiary alcohol, olefin. Product: nitrile, amide, amine, imine.

The Schmidt reaction is an organic reaction used to convert hydrazoic acid to a variety of products using an acid catalyst. The mechanism shown is for an aldehyde regent but it can be easily extended to the other regents. The reaction begins with abstraction of a proton from the acid by the aldehyde or other reagent to activate it for future attack. The generated water molecule then abstracts the proton from hydrazoic acid to regenerate the acid and produce an azide anion which then attacks the activated reagent. A series of steps and the release of a molecule of nitrogen gas result in the final product.[1][2]


Mechanism of the Schmidt reaction. Mechanism shown is for an aldehyde reagent.


Schmidt, K. F. Z. Angew. Chem. 1923, 36, 511
Schmidt, K. F. Ber. dtsch. Chem. Ges. 1924, 57, 704–706.