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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Nekromantis on March 05, 2013, 03:54:53 PM

Title: Preparation 3-Picoline-N-oxide
Post by: Nekromantis on March 05, 2013, 03:54:53 PM

Hi,

I'm student of organic chemistry from Poland. I need preparation 3 (or 2)-Picoline-N-oxide from Picoline. I can't find anything in polish students materials :(

Please, help

Title: Re: Preparation 3-Picoline-N-oxide
Post by: Corribus on March 05, 2013, 04:00:21 PM

Oxidation of pyridine derivatives can usually be effected very easily and in good yield and minimal difficulty with a peracid like meta-peroxybenzoic acid (mCPBA).  Even I, a physical chemist, could manage it. :)

I don't have a procedure handy, but I bet if you search for oxidation of pyridine or bipyridine with mCPBA, you should be able to adapt a procedure to picoline pretty easily.

...

Here's an older procedure.  I'd use mCPBA instead of the reagent used there.  It'll be much safer to handle.

http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0828

Title: Re: Preparation 3-Picoline-N-oxide
Post by: Dan on March 05, 2013, 05:53:11 PM

I have used this procedure (hydrogen peroxide/acetic acid) for the oxidation of 2-ethylpyridine before:

http://pubs.acs.org/doi/suppl/10.1021/ja028779v/suppl_file/ja028779v-2_s1.pdf

Title: Re: Preparation 3-Picoline-N-oxide
Post by: Nekromantis on March 06, 2013, 04:20:35 AM

Thank you very much ;)