Reactions of esters with nitrogen compounds

Two fundamentally different types of reaction of esters with ammonia and its derivatives must be distinguished, although in both cases oxygen is replaced by nitrogen  

With a few exceptions due to substitution,752 carboxylic esters cause acylation on nitrogen (as in A), but many mineral acid esters as well as arenesulfonic esters are powerful alkylation agents (see B). 

For the alkylation of amines by carboxylic esters in the presence of lithium tetrahydroaluminate see a paper by Wright.753 

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