# Preparing an amine from an azide

Is there any mechanism available for reduction of alkyl azides to amines. One of the reactions is conversion by $\ce{Na}$ in ethanol or by $\ce{LiAlH4}$. But how do these proceed? $\ce{LiAlH4}$ will produce a hydride ion which attacks where?

• Different reagents will have different mechanisms. Are you interested in one reagent in particular? – bon Jul 16 '15 at 17:20
• the ones I have mentioned i.e. Na in ethanol and LAH – Karan Singh Jul 16 '15 at 17:24

I googled it for a while and this was the best thing I found (Source):

This is a tough question, that is probably not known with any certainty. Even Jerry March (Adv Organic Chem, 4th ed, page 1219) doesn't commit himself to a mechanism.

You'll have to speculate. Add a hydride on the N next to the alkyl group, then grab a proton on the terminal N. Add a hydride on the terminal N, then grab a proton on the middle N. After that, it gets a little sketchy for breaking the N-N bond.

Try a SN2 attack by hydride on the middle N, giving hydrazine and RNH-, which is a lousy SN2 leaving group, but we're stuck with it. Protonation of the RNH- gives the amine and hydrazine. Or, you could do a SN2 on the N next to the alkyl group, and kick out a NH2NH- anion, which is also a lousy leaving group for the SN2. You can see why most books conveniently leave out a mechanism for this reduction.

• I don't see the mechanism on that link. Which page are you referring to exactly? – bon Jul 18 '15 at 18:09
• At the current state, this doesn't provide an answer to the question. Am flagging for deletion. – M.A.R. Jul 18 '15 at 18:23
• This is a better one, but it's highly encouraged (read: required) that you put the link to the source here. – M.A.R. Jul 23 '15 at 19:56
• I'm finding answers.yahoo.com/question/index?qid=20100525170905AA9PDiD as a source – austinian Jul 23 '15 at 21:20
• If you are quoting verbatim, always mention the source. I will insert it for now since @austinian already found it, but please avoid that in future answers. – Martin - マーチン Jul 24 '15 at 1:54