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Author: Subject: 2-picoline synthesis
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[*] posted on 29-12-2013 at 11:16
2-picoline synthesis

I'm interested in making 2-picoline (AKA 2-methylpyridine). The purpose is to use it to mono brominate the methyl using bromine and light, and then do the Sommelet reaction on this substrate to get picolinaldehyde. This compound could then be turned to the final product, the pralidoxime drug, an antidote to modern war gas. I don't think I will be attacked with war gas soon, but it is a nice goal for a chain of reactions.

I though I could do a field-craft onto pyridine and purify by distillation the 2-picoline. I wonder if that would be the easiest path.


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29-12-2013 at 11:58
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[*] posted on 29-12-2013 at 14:33

I don't think that will work. I believe you would protonate the N and develop a pyridinium-metal-Cl complex. The classic way is to make it from cyclohexylamine in NH3 with ZnCl in 40-50% yield (Merck).

check Ullmans: DOI: 10.1002/14356007.a22_399

the process was acetaldehyde in ammonia as with other Hantzch heterocylce synths

[Edited on 29-12-2013 by chemrox]

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[*] posted on 5-1-2014 at 01:06

Pyridine is more aromatic than benzene, Friedel crafts reactions do not work with pyridine. Its reactivity is often compared to that of nitrobenzene. Have a look at the chemistry of pyridine, and have a rethink.
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