Is there any reason why 2-Nitropropane would not work as a substitute for nitroethane in a nitroaldol (Henry) reaction?
I have a couple of patents which state that in place of nitroethane, nitropropane or a higher nitroalkane would also work for producing
phenylpropanols. But the patents don't state whether it is referring to 1-nitropropane, or 2-nitropropane.
I 'm hoping it is the latter, as I have found a cheap source for the stuff.
Thanks.Sergei_Eisenstein - 26-7-2007 at 12:34
As far as my knowledge reaches, both 1- and 2-nitropropane can be used as reagents for nitro-aldol condensations. There may be a difference in ease of
anion formation. After the necessary chemical manipulations, you may obtain phenylpropanol homologs.Hilski - 26-7-2007 at 14:50
That's good to hear, thanks.stoichiometric_steve - 28-7-2007 at 03:53
you are probably trying to make some amphetamine analogs. there, 2-nitropropane is of no use whatsoever.Hilski - 28-7-2007 at 14:25
Quote:
you are probably trying to make some amphetamine analogs. there, 2-nitropropane is of no use whatsoever.
Thanks for that info. Just for my own education, would you mind explaining why 2-nitropropane would be of no use in that scenario?
Thanks again.Blind Angel - 28-7-2007 at 14:31
wouldn't it make a phentermine analog?stoichiometric_steve - 29-7-2007 at 06:41
Quote:
Originally posted by Blind Angel
wouldn't it make a phentermine analog?
thats right.
hilsi,
if you cannot distinguish 2-nitropropane from nitroethane and their reaction products in the henry condensation, you should probably go and teach
yourself some basic organic chemistry.
most of the people posting questions like yours apparently think organic chemistry is matching names that sound similar (or similar enough, for that
matter).
fyi, it is NOT.
when you are trying to make a 9-carbon compound, it's obvious that if you make a 10-carbon compound it cannot quite be the same.
why do we have to go explaining this over and over?Hilski - 29-7-2007 at 07:46
Quote:
if you cannot distinguish 2-nitropropane from nitroethane and their reaction products in the henry condensation, you should probably go and teach
yourself some basic organic chemistry.
Yes, you're right about that.
Quote:
most of the people posting questions like yours apparently think organic chemistry is matching names that sound similar (or similar enough, for that
matter).
Well, that's not really the case here. The reason I even asked the question was because of what I read in THIS patent.
Quote:
when you are trying to make a 9-carbon compound, it's obvious that if you make a 10-carbon compound it cannot quite be the same.
OK. I now understand why it will not work. Thank you.
[Edited on 29-7-2007 by Hilski]Boomer - 29-7-2007 at 23:16
While you obviously cannot get phenyl-aminopropanes because of "one carbon too much", at least if starting with a substituted benzaldehyde, you might
get an interesting product.
I remember from Shulgin there were substitution patterns that gave bioactive molecules of all three, phenyl-amino-ethanes (PEAs), -propanes (amphs)
and -butanes. The latter could be called ethyl-phenetylamines or methyl-amphetamines, whatever you like more. These do have the extra carbon, and can
of course be made from nitropropane (at least 1-nitro).
Because you cannot cook meth with it, nitropropane might even be unwatched. On the other hand, with that terrorist hysteria, it might be watched
because Timmy with his ryder truck might substitute them for nitromethane Ullmann - 4-8-2007 at 06:30
Those butane compound are described in the ariadne entry #8 of pihkal. Tests on labrats showed them not to be hallucinogenic even at ten times the DOM
dosage. Sasha labelled them as antidepressant for old people as they tended to show remotivation in their daily activities while on it. They behave as
partial agonist of 5HT2A. Check JMC 1980 23 154. There is also a few patent about those compound on espacenet. On the old hive chimimanie made a review on this topic.
About the 2-nitro propane, after aldol reaction there is no way an elimination could take place hence you would be stuck with the nitro alcanol
instead of the nitrostyrene. On the old hive there was a method to get rid of that benzyl alcohol by acetylation then hydrogenation utfse the
archives.
