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I am working on a synthesis for a compound (4-aminophenol with alkyl chain and lactam at carbon 2). The final step of the synthesis involves hydroylsis of the secondary amide at carbon 4. My problem is I can not find a way to hydrolyse the secondary amide at carbon 4 without hydrolysing the lactam (which I don't want). Does anyone have any suggestions for how I could selectively hydrolyse the secondary amide? Thank you. Compound

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  • $\begingroup$ Is it really a problem if both the amide and lactam are hydrolyzed? Look at what you have left. $\endgroup$
    – user55119
    Nov 4, 2021 at 14:37
  • $\begingroup$ I cannot think of a way of doing this selectively. Either follow @user55119's advice or adjust the route at an earlier stage. $\endgroup$
    – Waylander
    Nov 4, 2021 at 21:41
  • $\begingroup$ How do you think that lactams are formed?@Waylander $\endgroup$
    – user55119
    Nov 4, 2021 at 21:45
  • $\begingroup$ @user55119 treatment of the fully hydrolysed material with a carbodiimide should give the lactam. I don't think either the phenol or aniline will interfere. $\endgroup$
    – Waylander
    Nov 5, 2021 at 8:27
  • $\begingroup$ @Waylander: I was hoping to get a response from the OP but alas. Or esterify the hydrolysis product and heat the bis-aminoester. $\endgroup$
    – user55119
    Nov 5, 2021 at 15:58

1 Answer 1

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Drawing on the comments of @user55119 above, I am going to to summarise the comments as an answer.

There is no way of selectively hydrolysing the acetanilide in the presence of the lactam.

It doesn't matter because the lactam can be readily reformed from the completely hydrolysed material by treatment with a carbodiimide such as 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The free phenol and aniline are unlikely to interfere as they are less nucleophilic than the secondary amine and you are forming a [5] ring with the lactam.

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