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Aromatic Diazotization of 3-aminopyridine

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Hey guys,

So I'm trying to do a diazotization of 3-aminopyridine (as the title has no doubt tipped you off), and I'm having some trouble. I'm dissolving the pyridine in excess of water, adding 1.2 env HCl and cooling the water in the flask with an acetone/dry ice bath down to -5ºC. I add NaNO2 in water dropwise to the flask but I don't see any redness or evolving gas, as I would expect to (so my PI says). After addition and enough time for homogenization, I reflux at 70ºC for several hours. The product does not form. Any ideas?

 

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A literature search suggests your conditions are too harsh. How are you tracking the reaction and working it up? I found a few references for you that cover the synthesis (you might have to look in the SI). If you have access to SciFinder or Reaxys, you can look these reactions up. 

 

 https://doi.org/10.1021/acsmedchemlett.9b00298

 
 
 

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