N,N-diethyl indole-3-acetamide
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Post 272175
(Ritter: "Re: Indole Grignards", Tryptamine Chemistry)Ritter says:
Diethylamine practically won't even react with the methyl ester, even when refluxed for 24 hours!
In Archiv der Pharmazie volume 275 pages 506-516 (1937) its gives a process for making indoleacetamide from ethyl indole-3-acetate and what seems to be strong ammonia solution. Its written in German. When diethylamine was substituted for ammonia there was no reaction even when tried at 200 degrees using a bomb tube.
Dimethylamine reacts. Why is there this difference with diethylamine?
See
https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleaceticacid.html