One pot reduction of b-nitro styrene to phenethylamine using sodium borohydride and copper 2 chloride

[jacksprat]

I came across this paper detailing the reduction of b-nitro styrene (not trans b-methyl nitro styrene} . this tweaked my interest due to the fact that Nitroethane is almost impossible to come by in the country I live but Nitromethane is . This paper is pretty new as it is listed as waiting on pier review.

Having no formal chem education but a fare amount of the clandestine type,, {its a lonely profession one cant exactly ask ones next door neighbor for advice who is a chemical engineer}

So my question is to those with a academic background is this.

The concept document goes like this. Henry reduction using benzaldehyde and nitromethane = b-nitrostyrene.
reduction to phenethylamine using sodium borohydride and copper 2 chloride (and a few other chems to make the catalyst}. Would it be possible to to add nitromethane to generate methylamine during the same reduction process as per the al/hg reduction.

Please shoot me down in flames if this a pipe dream


link to paper:

https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/65088cd1b6ab98a41caea11f/original/one-pot-reduction-of-nitrostyrenes-to-phenethylamines-using-sodium-borohydride-and-copper-ii-chloride.pdf

 

[Melv99]

I came across this paper detailing the reduction of b-nitro styrene (not trans b-methyl nitro styrene} . this tweaked my interest due to the fact that Nitroethane is almost impossible to come by in the country I live but Nitromethane is . This paper is pretty new as it is listed as waiting on pier review.

Having no formal chem education but a fare amount of the clandestine type,, {its a lonely profession one cant exactly ask ones next door neighbor for advice who is a chemical engineer}

So my question is to those with a academic background is this.

The concept document goes like this. Henry reduction using benzaldehyde and nitromethane = b-nitrostyrene.
reduction to phenethylamine using sodium borohydride and copper 2 chloride (and a few other chems to make the catalyst}. Would it be possible to to add nitromethane to generate methylamine during the same reduction process as per the al/hg reduction.

Please shoot me down in flames if this a pipe dream


link to paper:

https://chemrxiv.org/engage/api-gat...um-borohydride-and-copper-ii-chloride.pdf[/UR

jacksprat
Unfortunately no, Ch3No2 will not result in M-Amp AFAIK with that method. It was mentioned that It could be possible at the first post of a very large thread discussing this procedure elsewhere. But I've never came across anyone saying yes or no. From what I understand MeAm needs to form an imine with the Ketone under anhydrous conditions. Also, Ive read in some archived wrtieups, the imine does not form as well with the Ketone need for MEFF as it does with substituted Ketones(MD Variety).

Its possible but not one pot and many more steps to reach your goal unfortunately..

However, Ive never tried myself but as always i was curious so I decided to learn the mechanics of the reactions. Someone else may be able to explain better.[/url]

 

[G.Patton]

The concept document goes like this. Henry reduction using benzaldehyde and nitromethane = b-nitrostyrene.
reduction to phenethylamine using sodium borohydride and copper 2 chloride (and a few other chems to make the catalyst}. Would it be possible to to add nitromethane to generate methylamine during the same reduction process as per the al/hg reduction.

Please shoot me down in flames if this a pipe dream

jackspratIn theory, it's possible, but we haven't tried. You can try that and post here your results.
Pay attention that you need to carry out b-nitrosyrene synthesis at first and then add there nitromethane with additional counted portion of NaBH4 with catalyst.

 

[jacksprat]

In theory, it's possible, but we haven't tried. You can try that and post here your results.
Pay attention that you need to carry out b-nitrosyrene synthesis at first and then add there nitromethane with additional counted portion of NaBH4 with catalyst.

G.PattonOk, i might just give it a whirl. The question would be the volume of nitromethane to NaBH4, would that be similar to the well documented Al/Ag insitu reduction?

 

[OrgUnikum]

I came across this paper detailing the reduction of b-nitro styrene (not trans b-methyl nitro styrene} . this tweaked my interest due to the fact that Nitroethane is almost impossible to come by in the country I live but Nitromethane is . This paper is pretty new as it is listed as waiting on pier review.

Having no formal chem education but a fare amount of the clandestine type,, {its a lonely profession one cant exactly ask ones next door neighbor for advice who is a chemical engineer}

So my question is to those with a academic background is this.

The concept document goes like this. Henry reduction using benzaldehyde and nitromethane = b-nitrostyrene.
reduction to phenethylamine using sodium borohydride and copper 2 chloride (and a few other chems to make the catalyst}. Would it be possible to to add nitromethane to generate methylamine during the same reduction process as per the al/hg reduction.

Please shoot me down in flames if this a pipe dream


link to paper:

https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/65088cd1b6ab98a41caea11f/original/one-pot-reduction-of-nitrostyrenes-to-phenethylamines-using-sodium-borohydride-and-copper-ii-chloride.pdf

jackspratThats the Jademyr synth again.
Whats wrong with P2P + nitromethane/methylamine -> meth? BMK is cheaper then P2NP and you need much less NaBH4 too. So why?

 

[jacksprat]

Thats the Jademyr synth again.
Whats wrong with P2P + nitromethane/methylamine -> meth? BMK is cheaper then P2NP and you need much less NaBH4 too. So why?

OrgUnikumif you could point me in the direction of a bmk supplier that has reasonable pricing and ships to south africa that would be the answer. but the suppliers out of china and india are as dodgey as all hell and the ones listing on this forums pricing is so expensive it makes no sense on a commercial level. Or even a nitroethane, nitromethane is freely available here but no nitroethane and to synth it looks doable if one could get sodium ethyl salphate in quantities at good prices.