Aromatic amines are commonly used in the manufacture of dyes and pharmaceuticals.

Nucleophilic addition-elimination

This mechanism is nucleophilic substitution.

Aromatic amines such as phenylamine are prepared by reducing nitrobenzene. This is done by heating nitrobenzene under reflux with tin and concentrated hydrochloric acid to form the ammonium salt, phenylammonium chloride, which is then converted to phenylamine by a reaction with excess sodium hydroxide.

The equation for the preparation of phenylamine from nitrobenzene is:

Nitriles are reduced to primary amines by passing the nitrile vapour and hydrogen gas over a nickel catalyst.

For example, ethylamine is produced from the reduction of ethanenitrile:

CH₃CN + 4[H] ➔ CH₃CH₂NH₂

1. Nucleophilic substitution of a halogenoalkane using ammonia in ethanol.
2. Reduction of a nitrile using hydrogen and a nickel catalyst.

Halogenoalkanes are heated under pressure in a solution of excess concentrated ammonia in ethanol to form amines. A nucleophilic substitution reaction takes place.

For example, ethylamine is produced from the reaction of chloroethane and ammonia:

C₂H₅Cl + 2NH₃ ➔ C₂H₅NH₂ + NH₄Cl

In catalytic hydrogenation, the primary amine product does not react further, avoiding the formation of unwanted secondary, tertiary, and quaternary amines.

Secondary amides are prepared by reacting acid anhydrides with primary amines.

For example, N-methylethanamide can be prepared from ethanoic anhydride and methylamine

(CH₃CO)₂O + CH₃NH₂ ➔ CH₃CONHCH₃ + CH₃COOH

Primary amides are prepared by reacting acid anhydrides with ammonia.

For example, ethanamide can be prepared from ethanoic anhydride and ammonia:

(CH₃CO)₂O+ NH₃ ➔ CH₃CONH₂ + CH₃COOH