I,m trying to synthesis Schiff base ligand by using Diaminomaleonitrile and 2-Acetylpyridine and 2'Hydroxyacetophenone in 1:1:1 mole ratio in two steps.
but i have problem to synthesis the first step ( 2Acetylpyridin+Diaminomaleonitrile). the condensation of ketone and diamine never happend even with 1,4 Dioxan, and even with 1:2 mole ratio.
could you please suggest me appropriate solvent or catalysts or anything that would be helpful?
According to the literature you have to use acid catalysis and even you can run the reaction in water. Section 9 (page 28) Compounds 82,83,84
you must do the condensation reaction in acidic condition for synthesis of half unit of ligand.
Dear Elham,
Your synthetic problem is not so easy.You may find a lot off paper with condensation of aliphatic amines with aromatic ketone but they do not working. Bearing in the mind that pyridine as catalytic poison for H+ acids.In your case may be some Lewis acid will be good choice but,also you must be carefully with metals ion because your substrate have a lot off nitrogen as potential ligand.
Secound, try reaction on mortar with pastle with heating without any catalyst or with Lewis acids.
Best,
Nenad
Condensation of Diaminomaleonitrile and 2-Acetylpyridine prefer monoimine product. By use simple solvent such as methanol or ethanol you can get easily such product.
For more use this reference link
Article Copper(I) complexes of 2-(benzen-1-yl)methyleneamino-3-amino...
Reaction of of Diaminomaleonitrile and 2-Acetylpyridine in methanol or ethanol easy in presence of acid or base catalyst . Simply by stirring one can get the product .You can carry out this reaction under microwave irradiation.
Dear Elham, condensation of amines with ketones is favoured either with an acid or a base at room temperature or at higher degrees. But in yours case the problem may be arouse due to 2-acetyl pyridine. Check the solubility of the starting materials and conversion of starting material using various systems. Else prefer another substrate to let know the reactivity and then proceed with your targeted ones.
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