# Why doesn’t aniline undergo Friedel-Crafts alkylation?

Even though aniline is an activated benzene derivative, it still doesn’t undergo Friedel-Crafts alkylation. Why?

Can it undergo Friedel-Crafts acylation?

The answer lies in the fact that aniline is a Lewis base and $\ce{AlCl3}$ is a Lewis acid. The reaction between aniline and $\ce{AlCl3}$ hampers the catalytic activity of $\ce{AlCl3}$ required to perform the Friedel-Crafts alkylation and acylation.
Despite the activation of the $\ce{NH2}$ group, Friedel-Crafts alkylations and acylations fail because the $\ce{NH2}$ group acts as Lewis base and interacts with the Lewis acid catalyst. ... A way to overcome this problem is to convert the $\ce{NH2}$ group into an amido group prior to Friedel-Crafts reaction. ...The amide group can be hydrolysed back to aniline group after alkylation.
The aniline forms a Lewis acid base adduct with $\ce{AlCl3}$ :
This prevents the interaction between alkyl or acyl chloride with $\ce{AlCl3}$.