Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: 2-picoline synthesis
plante1999
International Hazard
*****




Posts: 1937
Registered: 27-12-2010
Member Is Offline

Mood: Mad as a hatter

[*] 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.

Thanks




I never asked for this.
View user's profile View All Posts By User
Nicodem
Super Moderator
Thread Moved
29-12-2013 at 11:58
chemrox
International Hazard
*****




Posts: 2930
Registered: 18-1-2007
Location: UTM
Member Is Offline

Mood: psychedelic

[*] 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]




"Ignorance is the Mother of Devotion." — Robert Burton.
View user's profile View All Posts By User
eidolonicaurum
Hazard to Self
**




Posts: 71
Registered: 2-1-2014
Location: Area 51
Member Is Offline

Mood: Hydric

[*] 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.
View user's profile Visit user's homepage View All Posts By User

  Go To Top