i want to get an N-substituted pyridone with the fonction -COOH, so i tried the reaction between Pyridone and Hexanoic acid in tetrahydrofuran with K2CO3 to deprotonate the pyridone. If the N-substituted pyridone with the fonction -COOH is insoluble in the reaction medium but soluble in water, is there any way to purify it.
For the base i dont dispose on NaH or Li bases, so is there any others more convinient for this synthesis.
Its depends on the quantity are looking for.
milligrams scale, you can go with prep HPLC (using ammonium acetate buffer).
Few grams go with glass column by using dichloromethane + Methanol mixture
For higher scale, better we can go with recrystallization
Article Regioselective synthesis of C-2 substituted imidazo[4,5-b]py...
DOI: 10.1039/c3nj01355c
Hi
Firstly, I am not sure if the pyridone nitrogen will react with the acid in the presence of the base. At the very least it seems you need a more reactive carboxyl group.
Secondly, purification depends on what is in the reaction mixture and the solubilities of the product and the impurities in different solvents.
You need Br（CH2）n COOR，the ester， not the acid for your reaction！ Then it will be easier to be purify by silica gel column！
Sandeep Chandrashekharappa. I want to get the N-substituted pyridone with -COOH fonction on the N of it, that is why i used 6-bromohexanoic acid for the substitution reaction in basic environment. besides the low yield, i could not purify the product because it was water soluble.
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