Spezialemic Posted March 3, 2020 Share Posted March 3, 2020 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? Link to comment Share on other sites More sharing options...
hypervalent_iodine Posted March 3, 2020 Share Posted March 3, 2020 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 https://doi.org/10.1002/chem.201902150 https://doi.org/10.1002/jhet.3686 https://doi.org/10.1002/slct.201803039 Link to comment Share on other sites More sharing options...
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