Sciencemadness Discussion Board

Nicotine to Pyridine ?

Korialstrasz69 - 17-3-2016 at 06:34

Ya'll
I can't find anything about it because i would guess no one really gives a shit about it normal people can reqest that online, but just out of curiousity is it possible ? And what's the reaction called/What's the mechanism?

fluorescence - 17-3-2016 at 09:20

Yes.

One way is by Weidel in "Justus Liebigs Annalen der Chemie, 1873 , vol. 165, p. 346" but I dont have that paper to tell you how he did it and its really old. They use Chromium(III)Oxide, Sulfuric Acid and Bromine water under heat.

Another one by Leiblin "Chemische Berichte, 1877 , vol. 10, p. 2136" here they use Permangate in the first step

And one by Leete "Phytochemistry (Elsevier), 1985 , vol. 24, # 5 p. 957 - 960". That one is on the net called
"SPERMIDINE: AN INDIRECT PRECURSOR OF THE PYRROLIDINE RINGS OF NICOTINE AND NORNICOTINE IN NICOTIANA GLUTINOSA"

It says here

1) Nitric Acid
2) CaO + heat


I can look into the paper:

It won't really copy paste so I give you a screenshot of that paper

For the mechanism I need some time to think of one but those are the only papers that deal with this topic.



[Edited on 17-3-2016 by fluorescence]

Nicotine.JPG - 76kB

Delta - 17-3-2016 at 19:29

My question is (and it only pertains if your question is directed towards practical means), how much nicotine are you willing to work with, let alone buy? If you plan on actually undertaking this, might I recommend niacin as a starting material instead? Certainly more economical, and less oxic.

Korialstrasz69 - 17-3-2016 at 23:15

No i am not willing to practice this. But if i were to i would extract nicotine in a few portions under a fumehood, reacting each batch into niacin before moving on to the next