These reductions on ring-substituted nitropropenes do work.
But,they usually don't work very well. Yields can be downright crappy. Zed had a friend that tried all kinds.
Different rings=Different yields. Unfortunately, these were
never really "Happy Yields".
As for LiAlH4, you are wise. Zed's friend made a few buildings disappear with this fine product. Especially great when used in diethyl ether.
As for hydrogenation; Well, I think you may be missing something. Your hydrogenation experiments have produced
P2P-Oxime. Hydrolyse and extract, or steam distill
the resulting P2P from your solution. This P2P can then be
reductively aminated to form whatever N-substituted Phenyl-
isopropyl amine you choose. Now, if you must have a one step reduction from phenyl-nitropropene to amine, or you must have the unsubstituted amine...This won't work for you. If you are a practical man, you are already at the
top. You know how to use hydrogen! I'm sure you are familiar
with Heinzelman's proceedure for reductively aminating ketones. For legal reasons, I am not suggesting you use it.
But, in my opinion, variations on than method, in conjunction with your already achieved P2P synthesis, form
an unbeatable combo.. Keep in mind, the reduction of the
aforementioned nitro-propenes with Pt in acid solution, is
quite rapid. It workes well at STP. So well, that an ordinary filter flask, with magnetic stirring, could work well as a reaction vessel. Further, the catalyst might be able to reduce as many as 20 charges of solvent/nitropropene
in sucession... If you were to siphon off each portion at
the completion of reaction, and then siphon in fresh reactant....while leaving the vessel sealed. In short it is
an industrial type reaction. Small reaction vessel, great yield, lots of product. So as I stated in another post!
There is no higher or further, you have achieved your goal.
Do you think it might be time to do something else?
