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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: pinkman on January 26, 2020, 12:57:20 PM

Title: Cyanopyridine
Post by: pinkman on January 26, 2020, 12:57:20 PM

I want to introduce a cyano group at the 3- position of a pyridine. I also need an amino group at the 4- position.

I thought about starting with 4-hydroxy pyridine, then doing a bromination to end up with a bromo derivative at the 3- position. But then, all the papers i find need some kind of palladium catalyst for the Br to CN conversion but I dont have any. Is there any other way?

For the OH to NH2 conversion I am thinking about using phosphorous pentachloride (Cl at the 4- position) and then ammonia to yield the amino derivative.

I dont have any other substituted pyridine derivatives for starting material.

Title: Re: Cyanopyridine
Post by: rolnor on January 26, 2020, 02:19:43 PM

The 3-position is not activated so I think you need catalyst, I think people use Pd and ZnCN2? If you have the CN and do a triflate in the 4-position you get something that react fast with NH3. I would do a literature search on the your compound and then buy the startingmaterial they use, this project could be expensive and take long time.