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Clarke-Eschweiler reaction

Started by PEYOTE, June 18, 2000, 10:27:00 PM

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PEYOTE

June 18, 2000, 10:27:00 PM
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

#1
June 18, 2000, 10:33:00 PM
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

#2
June 18, 2000, 10:35:00 PM
But not for tryptamines, since they will cyclize to beta-carbolines under this conditions (Pictet-Spengler reaction)  :( .

PEYOTE

#3
June 18, 2000, 10:51:00 PM
I'd like to know more of this cyclization..... thanks...

Rhodium

#4
June 19, 2000, 12:08:00 AM
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.
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