Sciencemadness Discussion Board

4-Methylpyridine

Huk40 - 28-3-2011 at 02:51

I want to synthesize that compound,but I can't seem to find any information on it's synthesis.I need it for the preparation of Brooker's merocyanine (1-methyl-4-[(oxocyclohexadienylidene)ethylidene]-1,4-dihydropyridine, 'MOED') .Any ideas?

ScienceSquirrel - 28-3-2011 at 04:00

It is isolated from coal tar and made on an industrial scale and readily available so most chemists would not bother making it.

http://en.wikipedia.org/wiki/4-Methylpyridine

Look in the sweetie shop window! :(

http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en...

Huk40 - 29-3-2011 at 00:42

I'm from Bulgaria,and here I can't find any firm that I could buy it from.

ScienceSquirrel - 29-3-2011 at 02:56

If you cannot buy 4-methylpyridine you will probably find it hard to buy the chemicals needed to make it.
The industrial synthesis from acetaldehyde and ammonia is easy and cheap to run but low yielding, requires serious gear and major purification of the product.

Aqua-regia - 29-3-2011 at 13:14

Read this patent. If you have electric pipe-furnace and NH3 cylinder, than it is piece of cake.

http://www.wipo.int/pctdb/en/wo.jsp?WO=2005%2F063389&IA=...



[Edited on 29-3-2011 by Aqua-regia]

Picolin.jpg - 69kB

ScienceSquirrel - 30-3-2011 at 04:06

You might just be a little beyond the resources of the average shed chemist there! :D

Mindchemist - 5-4-2011 at 17:44

I think 4-cresol and ammonia will work, though it would probably need a catalyst.

jon - 5-4-2011 at 19:14

why 4 methyl?

ScienceSquirrel - 6-4-2011 at 02:21

Quote: Originally posted by Mindchemist  
I think 4-cresol and ammonia will work, though it would probably need a catalyst.


Not a chance! :P

GreenD - 6-4-2011 at 06:31

GOOD QUESTION. :D

Mindchemist - 9-4-2011 at 15:59

You could try 4-cyanopyridine and methyl iodide, though it would also release cyanogen iodide if the reaction would go as I expect. You could do the reaction in a hydroxide solution to detoxify the cyanogen iodide to a iodide and isocyanic acid.

[Edited on 3-27-2011 by Mindchemist]

Mindchemist - 10-4-2011 at 16:42

http://en.wikipedia.org/wiki/4-Picoline

Might be useful.