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Topic: methylamine reaction with formaldehyde cyanohydrin  (Read 3237 times)

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Offline Tosyl1

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methylamine reaction with formaldehyde cyanohydrin
« on: December 27, 2010, 01:33:31 PM »
Hey,

Can anybody help with this reaction:

methylamine + formaldehyde cyanohydrin => N-methyliminodiacetic acid.

It seems that amine is reacting with hydroxyl group, then, subsequently, the methyl imino dinitrile is hydrolysed. But what is the mechanism for OH=>NH2 substitution? Any hints?
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Offline Trave11er

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Re: methylamine reaction with formaldehyde cyanohydrin
« Reply #1 on: December 27, 2010, 01:52:09 PM »
In acidic medium formaldehyde cyanohydrin could drop HCN to form formaldehyde which is then attacked by amine to form imine - the latter is attacked by CN- and the required product is botained after hydrolysis.
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Offline Tosyl1

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Re: methylamine reaction with formaldehyde cyanohydrin
« Reply #2 on: December 27, 2010, 02:59:02 PM »
Hmm, that would be similar to Strecker amino acid synthesis. Thanks
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