Ethlenediamine….

Rabidreject

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Would this be an appropriate catalyst over methylamine HCL for a Henry reaction?
I do have ammonium acetate which is my first go to, however, I’m aware you need more nitromethane with that route which is hard to get and expensive…

My guy who can basically get anything from sigma-Aldridge (primarily) said to me (when I purchased a custom order of 40% w/w nitromethane:DCM - that’s a shipping and explosives thing though), noticed I was asking about his methylamine HCL (honestly I figured it may be useful at some stage if I ever decide to fuck with the mdma or basically methylene-dioxy compounds….one day. I’m a compound collector - active an inactive, he said to me ‘if you are planning on doing a Henry reaction, we have ethlenediamine - where as our methylamine is HCL so the prior would be a better catalyst’

It makes sense to me - I currently have 2,5-dimethoxybenzaldehyde but plan to get a larger quantity of 3,4,5-trimethoxybza - so I’ll need a half decent supply of nitromethane but If I can cut the amount that would be useful!
As I’m a collector I did decide to get some of the ethlenediamine whilst it’s still in, seems like the methylamine Hcl is pretty standardly in stock.
What do we think?
 

FENTAMAS

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Ethylenediamine diacetate is one of the best confirmed catalysts for the condensation of 2,5-DMBA with MeNO2,
giving nitrostyrene yield over 90%, even if prepare it in situ from diamine and dry acetic acid.
So your choice is right.
 

Rabidreject

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Yiiiiiiiis… this is what we like to hear (mwahahaha rubs hands as evil plan comes together) JK
BUT it does give me a seperate option over ammonium acetate and GAA, in which I believe you end up using more of the MeNO2 - which is expensive and annoying to obtain.
Cool - thanks for your reply! V useful….this is one that’s been on the back burner as I been gathering some 2,5-DMOBA - just a small amount - 50g and even some LiAlH4, which I know everyone is trying to move away from and towards borohydride but I had to try it at least a couple times with LAH! This new supplier is useful lol
 
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