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: 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.
