Nitro reduction and basification
Nitrobenzene gives aniline through nitro reduction and basification.
- Reagents
- Tin / hydrochloric acid; then sodium hydroxide
- Conditions
- Acidic reduction followed by alkaline work-up
- Reaction class
- Nitro reduction and basification
- Equation
- C6H5NO2 + 6[H] -> C6H7N + 2H2O
Overview
Nitrobenzene gives aniline through nitro reduction and basification.
Transformation
- Equation
- C6H5NO2 + 6[H] -> C6H7N + 2H2O
- Reagents
- Tin / hydrochloric acid; then sodium hydroxide
- Environment
- Acidic reduction followed by alkaline work-up
- Reaction class
- Nitro reduction and basification
- Mechanism
- nitro reduction and basification
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- Named nitrobenzene example; not a class-wide route prediction.
- Limitations
- Acid first gives phenylammonium ions. Free aniline requires basification. [H] is formal reducing equivalents, not hydrogen gas; tin salts and work-up species are omitted.
Related reactions
- Nitration: Benzene → Nitrobenzene
Benzene gives nitrobenzene through nitration.
- N acetylation: Aniline → Acetanilide
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.
References
- Preparation of phenylamine (aniline)Jim Clark · Chemguide · 2016
Named molecular transformation examples, checked 2026-09-08.