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Reducing 3,4,5-trimethoxy-beta-nitrostryrene to mescaline by Matilda Bomblehit - Wed, 13 Jun 2018 11:03:55 EST ID:rajg/xs8 No.79145 Ignore Report Quick Reply
File: 1528902235968.png -(5534B / 5.40KB, 460x300) Thumbnail displayed, click image for full size. 5534
I want to reduce 3,4,5-trimethoxy-beta-nitrostyrene to the amine. What will do this? I've found so much worthless and bullshit information. It seems the main options are:

  1. Zn/HCl or Fe/HCl. I don't know if this goes from the nitrostyrene to the amine or if I need to use NaBH4 to first reduce the double bond. Also, some people say the yields are good and others say the yields are shit.

2. LAH. Not an option.

3. SnCl2 to reduce the nitrostyrene to an oxime and then Zn to reduce the oxime to the amine. I've never found proof of anyone doing this reaction on nitrostyrenes. SnCl2 is good for reducing nitropropenes but who knows if that applies to nitrostyrenes.

4. Al/Hg. Literally toxic. I haven't found any reports of people using the less toxic Al/Ga or Al/Cu amalgam. I also get conflicting information saying Al/Hg reduces directly to the amine, yet others are saying NaBH4 must be used to first reduce the double bond and then the Al/Hg reaction can be run to reduce the nitro group to an amine -- which is it?

Any input would be appreciated, especially from people who have actually run these reactions on this particular substrate.
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press - Thu, 14 Jun 2018 15:10:21 EST ID:Hu9hjiL2 No.79146 Ignore Report Quick Reply
whats "literally toxic" as opposed to toxic?
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Phoebe Wicklefoot - Wed, 20 Jun 2018 13:34:12 EST ID:f7Wsgp11 No.79148 Ignore Report Quick Reply
>>79145
Are you planning on making larger quantities? if not, just go with al/hg. use your common sense and everything will be fine. solubility of mercury salts in organic solvents is negligible. when you worry about the organomercury compounds, just give your product (salt) a proper wash with organic solvents and acetone and you are golden
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Archie Duckstone - Tue, 21 Aug 2018 22:59:51 EST ID:zbIVdkqy No.79213 Ignore Report Quick Reply
fucking crush it with hot hydrogen
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Samuel Turveydock - Wed, 22 Aug 2018 20:39:00 EST ID:zbIVdkqy No.79215 Ignore Report Quick Reply
>>79148
pushing it through a pad of celite or silica would help but honestly there isnt any reason to go with mg or tin
ochem portal has a page dedicated to conjugated nitro reductions...
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Martin Drablingville - Thu, 23 Aug 2018 15:55:31 EST ID:quGHpYNb No.79217 Ignore Report Quick Reply
Zn/HCl is the method of choice for terminal nitrostyrenes, but it fails for nitropropenes. Fe/HCl gives carbonyl compounds which you don't want. Make sure your zinc is good.
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Bombastus Werrywag - Sat, 20 Oct 2018 04:35:52 EST ID:L5efXmCV No.79258 Ignore Report Quick Reply
>>79217
double bond may prevent the latter but either sources of hydrogen should work. then introduce it with palladium on carbon under a little party balloon to give you the pressure required to hydrogenate that 2nd position


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