Pumukli - 11-3-2016 at 05:53
Some SM members are efficiently promoting the prepchem website, so efficiently that finally I also registered and browsed the site "just for fun".
While I was checking the various preparations I came across a synthesis of diethylamine which I found strange and intriguing.
It starts from N,N-diethylaniline and treats it with NaNO2/acid in the first step (making p-nitroso-aniline) then in a second step this
nitroso compound is treated with NaOH and boiled/distilled. In the distillate there is diethylamine with a good yield.
Could someone shed light on the mechanism of this 2nd step reaction? Is it a simple nucleophilic substitution? A nitroso group makes it (obviously)
possible but does it mean that another EWG (e.g. nitro or CF3 group) would be OK in the 4-position or am I overlooking something? What
remains in the pot? p-nitroso-phenol sodium salt?
Thanks for the help!
Pumukli - 11-3-2016 at 10:37
Meanwhile I found this reaction described in Organikum. Apparently it is a well-known (and important) synthesis method of aliphatic secondary amines
according to the book.