Reduction of nitriles to primary amines with LiAlH4

by James

Description: Lithium aluminum hydride [but NOT sodium borohydride (NaBH4)] can reduce nitriles to primary amines.
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{ 4 comments… read them below or add one }

Kapil May 31, 2012 at 6:19 am



Matthew Granger January 22, 2015 at 7:09 pm

For step 2. Instead of N- getting a second negative charge N (2-), would it first protonate itself once? and then repeat from there until it left?


James January 26, 2015 at 5:13 pm

Hey Matt – although N is drawn with a second negative charge in practice it will be bound to aluminum [an excellent Lewis acid], and the Al-N bond will be quite strong so it’s not as “naked” as it appears. There aren’t really any proton sources present to protonate the nitrogen at this stage until workup.


Matthew Granger January 26, 2015 at 5:31 pm

Yeah, that makes sense, basically the electron density of N is being donated to Al, resulting in less anionic nature as observed.
Thanks James!


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