In the hydrolysis of Phthalimides we can see two successive hydrolysis of "amides" see ChemLibre for a nice mechanism

This is interesting because normally (also according to ChemLibre) amides are very stable (the amine is a poor leaving group) and don't react.

Nevertheless the first hydrolysis can be rationalized because the nitrogen electrons are delocalized and there is ring strain. Similar to how beta-lactams are more reactive than normal amides.

However, the second reaction appears to be just a normal amide hydrolysis. How does this happen?

  • 3
    $\begingroup$ Generally under forcing conditions. Elevated temperature, concentrated reagents and long reaction times. $\endgroup$
    – Waylander
    May 14 at 9:07
  • $\begingroup$ It is normal amide hydrolysis, so I don't get why you're asking. $\endgroup$
    – Mithoron
    May 17 at 17:46


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