Post 272175 (https://www.thevespiary.org/talk/index.php?topic=12941.msg27217500#msg27217500)
(Ritter: "Re: Indole Grignards", Tryptamine Chemistry)
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 (https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleaceticacid.html)