PEYOTE (Newbee)
06-18-00 22:27
No 18616
       Clarke-Eschweiler reaction  Bookmark   

To obtain N,N-dimethyl alkanes form R-NH2, you can use the reaction of Clarke-Eschweiler
using HCOOH and CH2O in polymeric form....

  
 
 
 
    Rhodium
(Chief Bee)
06-18-00 22:33
No 18619
       Re: Clarke-Eschweiler reaction  Bookmark   

This won't work with tryptamine. Formaldehyde and acid will lead to a pictet-spengler cyclization, forming a beta-carboline.

http://rhodium.lycaeum.org 		 
 
 
 
    Lilienthal
(Moderator)
06-18-00 22:35
No 18620
       Re: Clarke-Eschweiler reaction  Bookmark   

But not for tryptamines, since they will cyclize to beta-carbolines under this conditions (Pictet-Spengler reaction) frown.

  
 
 
 
    PEYOTE
(Newbee)
06-18-00 22:51
No 18628
       Re: Clarke-Eschweiler reaction  Bookmark   

I'd like to know more of this cyclization..... thanks...

  
 
 
 
    Rhodium
(Chief Bee)
06-19-00 00:08
No 18640
       Re: Clarke-Eschweiler reaction  Bookmark   

Like this, http://home.ici.net/~hfevans/reactions/RXN300.htm but instead the new carbon-carbon bond is formed between the formaldehyde imine and the 2-position of the indole nucleus.