Amide Synthesis
Amides are commonly formed via reactions of a carboxylic acid with an amine. Many methods are known for driving the unfavorable equilibrium to the right:
- RCO2H + R'R"NH RC(O)NR'R" + H2O
For the most part, these reactions involve "activating" the carboxylic acid and the best known method, the Schotten-Baumann reaction, which involves conversion of the acid to the acid chlorides:
| Reaction name | Substrate | Details |
|---|---|---|
| Beckmann rearrangement | cyclic ketone | reagent: hydroxylamine and acid |
| Schmidt reaction | ketones | reagent: hydrazoic acid |
| nitrile hydrolysis | nitrile | reagent: water; acid catalyst |
| Willgerodt-Kindler reaction | aryl alkyl ketones | sulfur and morpholine |
| Passerini reaction | carboxylic acid, ketone or aldehyde | |
| Ugi reaction | isocyanide, carboxylic acid, ketone, primary amine | |
| Bodroux reaction | carboxylic acid, Grignard reagent with an aniline derivative ArNHR' | |
| Chapman rearrangement | aryl imino ether | for N,N-diaryl amides. The reaction mechanism is based on a nucleophilic aromatic substitution. |
| Leuckart amide synthesis | isocyanate | Reaction of arene with isocyanate catalysed by aluminium trichloride, formation of aromatic amide. |
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