Sciencemadness Discussion Board

Niacin ---> Pyridine (HCl)

ChemicallyImbalanced - 14-12-2004 at 16:52

Is it possible to remove the carbamoyl group from Niacin and rearrange its ring structure to give Pyridine? I assume this cannot be done, but if it can how would I go about doing so?

Marvin - 14-12-2004 at 20:06

Yes, this has been covered at E&W, and possibly here as well. Usual NaOH/CaO method should work but the beta carboxylic acids are rather more stubborn than alpha or gamma. I dont think anyone has tried the method yet.

Esplosivo - 14-12-2004 at 23:37

If you're about to prepare pyridine, and you're male, I would check out the MSDS. Pyridine can do some nasty things to your reproductive system in large enough conc. Take the necessary precautions. Just an advice.

ChemicallyImbalanced - 15-12-2004 at 14:10

I searched the forum here and didn't find anything on this, but where is E&W? Do you have any refs for this procedure? I searched all over and couldn't find anything of this nature. I did find many papers and patents about the reverse process though. Mostly 3-methyl Pyridine to Niacin and the like. I'm thinking a vigorous boil with 10% NaOH solution would do it. Any thoughts on that?


"Pyridine can do some nasty things to your reproductive system in large enough conc.”

I'm pretty much done laying my seeds. :D I doubt anyone would want to have my children anyway. :( :D


[Edited on 15-12-2004 by ChemicallyImbalanced]

The_Davster - 15-12-2004 at 15:34

E&W is www.roguesci.org

I believe this is the thread you want
http://www.roguesci.org/theforum/showthread.php?t=3289&h...

Marvin - 15-12-2004 at 17:03

Standard method for decarboxylation of an aromatic ring is to mix the acid with a large excess of CaO, or CaO and NaOH, or even just NaOH and destructivly distill. Organikum has a thread here on production of benzene from sodium benzoate or benzoic acid. Worth a read.

ChemicallyImbalanced - 16-12-2004 at 11:43

OK... thanks for the help.