A Novel route to ICE without BrCN??

[mayday]

A new method for making Methylaminorex (without CNBr) or PPA?

Some years ago I stumbled over the following syntheses:

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000172704-file_7mym.jpg" title="View this image">

If R1 is benzene and R is CH3 we would end up with 4-Methylaminorex and/or PPA!
I´m dreaming to take Isosafrol for this reaction (but I haven´t got some). This should be an interesting compound!
I could not get the original ref through my library. Maybe someone could post the text.
My question to all the chemists is: does the oxygen or the nitrogen moves to the benzylcarbon?
If this works, it could be an alternative method for making Methylaminorex without CNBr.

The orig. ref. is:
J.Takeda , S. Kuroda, J.pharm. Soc. Japan 1921, 467 ; 1921 I, 789

[LaBTop]

I think you can not see the picture :

Look at the next post, editted this double one out, costed me again 14 minutes to post that fucker, used Stop one time, that's the reason. LT/

[LaBTop]

I think you can not see the picture :

R1-        R1---Br
   ||           |
   || + Br-Br -->      |
   ||           |
R--         R---Br
 
 
 
R1---Br           O       R1---O
   |          | |          |  \
   |      +       | |       -->       |   NH2
   |         /   \                | //
 R---Br      H2N   NH2     R---N
 
 
 
R1---O                 R1---OH
   |  \                   |
   |   NH2 +  HO-  -->    |
   | //                   |
 R---N                  R---NH2

or visit the webpage picture at geocities, you can't link anymore to a pic there, you must give the url :

http://www.geocities.com/mayday007us/Methamrex.jpg

LT/

PS : when I posted this, a window popped up when I opened the post window, and "This window has both secure and insecure items in it, do you want to show the insecure items too?" popped up. I granted permission, and suddenly the picture appeared in the originator post window down there.
This insecure item (the pic) is probably the reason why we can't see those Geocities pictures linked here. LT/

WISDOMwillWIN

[mayday]

I´m really sorry LaBTop!
It was the first time ever, I´ve posted a picture into a Forum!

[LaBTop]

What, you get impressed by some red letters? Are you crazy, that was not meant to embarresh you, that was meant to help you!
That looks like a plausible idea, and deserves attention, that's why I tried to help you out, you timid piece of chickenshit.  
We propagate opinionforming like that, don't get intimidated by some "bigshots".
Rhod, Os, any answer for the "kid"? LT/

WISDOMwillWIN

[mayday]

I´m growing!
Do you have the ref.?!

[LaBTop]

Main online Frame Chemistry Journals list :

http://fg702-6.abct.polyu.edu.hk/~kmleung/journalm.html

and look at the top of the Newbee forum for my patent search post.
Esp@aceNet has a link to Japanese patent search. Use worldwide search.LT/

Or one of my assistants here, who is a pro in ref searching and translating, will stumble over it hopefully.
WISDOMwillWIN

[foxy2]

This is VERY interesting!!!
More info please
 

Do Your Part To Win The War

[jim]

I don't see the reference on that page.  I even went to the library, but my library doesn't carry that journal that far back in history.

I am very interested in this.  Has anybody figured out the sterochemistry?

[magic]

interesting, there may be a problem with bromination of the bezene ring in the 4 pos for plain propenyl benzene, or bromination in the pos next to the side chain in isosafrole however I believe the dibromo derivatives of sfrole and isosafrole are known compounds (the dibromo derivative of safrole having been used for ident of safrole in the good old days).

[psychokitty]

Does anyone think that pemoline could be reduced into aminorex?  It's just one carbonyl group away and OTC in some countries. 

Also, why is everybody so uptight about using CNBr to convert PPA into methylaminorex?  CNBr can be made in situ in methanol using sodium cyanide and bromine.  As long as some care was taken the proceedure shouldn't present that much difficulty or danger.  For more details, refer to Poos original US patent. 

--PK