N acetylation
The aniline nitrogen attacks an anhydride carbonyl and displaces an acetate-derived leaving group. Proton transfer forms acetanilide and ethanoic acid; attachment to C=O makes the product nitrogen an amide nitrogen.
- Reagents
- Ethanoic anhydride
- Conditions
- Controlled acylation of the amine
- Reaction class
- N-acetylation
- Equation
- C6H5NH2 + CH3COOCOCH3 -> C6H5NHCOCH3 + CH3COOH
Overview
The aniline nitrogen attacks an anhydride carbonyl and displaces an acetate-derived leaving group. Proton transfer forms acetanilide and ethanoic acid; attachment to C=O makes the product nitrogen an amide nitrogen.
Transformation
- Equation
- C6H5NH2 + CH3COOCOCH3 -> C6H5NHCOCH3 + CH3COOH
- Reactants
- Aniline + Acetic anhydride
- Products
- Acetanilide + Ethanoic acid
- Reagents
- Ethanoic anhydride
- Environment
- Controlled acylation of the amine
- Reaction class
- N-acetylation
- Mechanism
- nucleophilic addition-elimination
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- Aniline nitrogen receives an acetyl group.
- Limitations
- The product is an amide; its nitrogen no longer has ordinary aniline basicity.
Related reactions
- Nitro reduction and basification: Nitrobenzene → Aniline
Nitrobenzene gives aniline through nitro reduction and basification.
References
- Organic Chemistry: Chemistry of Acid AnhydridesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.