A chichibabin reaction of aromatic aldehyde with aromatic ketone and ammonium acetate was charged in acetic acid. Upon completion of reaction, it was washed with cold water. After filteration, the obtained precipitates were found not soluble in DCM, dioxane, benzene, THF, Acetic Acid, MeOH, ETOH, DMSO, DMF,ETOAc, Hexane. Could someone be kind enough to guid me how to make it solubilize so that i can moniter it on TLC for purity purpose? Thanks in advance.
Is the aryl ketone a diaryl ketone or a alkyl aryl ketone. The reaction does not appear to be a chichibabin reaction at all (uses pyridine and amide anion).
Dear Kirk Abbey, It is alkyl aryl ketone and aryl aldehyde. Solubility is a problem.
This appears to be a crossed Aldol reaction and not a chichibabin reaction. The product would be a chalcone (a 1,3-diphenylprop-2-en-1-one with whatever substituents your materials have). While the base chalcone is listed as being soluble in chloroform, ether, and benzene, your particular species may vary greatly. The alpha-beta unsaturated ketone may have stability issues such as succeptability to polymerization or nucleophilic addition. If a polymer, solubility may be very poor or take a long time to dissolve.
You may find this article of interest: http://www.jcbsc.org/admin/get_filechem.php?id=178
Now i see, it was my mistake earlier, i am sorry. Its not simple Aldol, it include Aldol condensation/Michael addition/ammonia-ketone condensation and reduction to form triarylpyridines, transformation called modified Chichibabin pyridine synthesis.
Nevertheless, triarylpyridines should be soluble in toluene or some similar aromatic solvent, try heating. Or try recrystalize it again from acetic acid for example, adding MeOH.
Dear Tahseen, you can try with toluene, or with mixing of solvent, an example is MetOH-DCM 10%, but if it's a polymer the product is less soluble.
Hi Taheseen iqbal
This is not chichibabin reaction.It is formed bi aryl imidazole.Aryl aldehyde and aryl ketone in presence of Ammonium acetate forming bi aryl imidazole.It is Soluble in Toluene and Acetonirile.Pls once check.It is definetly soluble
Regard
nagaraju.p
Dear Taheseen iqbal
From Wikipedia, the free encyclopedia: The Chichibabin reaction (pronounced ' (chē')-chē-bā-bēn) is a method for producing 2-aminopyridine derivatives by the reaction of pyridine with sodium amide. It was reported by Aleksei Chichibabin in 1914. So, this is not chichibabin reaction.
Dear Taheseen iqbal
Please, find in attach a paper on: Ceric ammonium nitrate (CAN) catalyzed one-pot synthesis of fully substituted new indeno[1,2-b]pyridines at room temperature by a
multi-component reaction by: Pradip Kumar Tapaswi and Chhanda Mukhopadhyay. ARKIVOC 2011 (x) 287-298.
Abstract
Ceric ammonium nitrate (CAN) (10 mol%) in ethanol has been found to be an efficient catalyst for the one-pot multi-component synthesis of fully substituted new indeno[1,2-b]pyridines through a combination of 1,3-indandione, propiophenone or 2-phenylacetophenone, aromatic aldehydes, and ammonium acetate at room temperature. The same methodology also worked well for the construction of several other 2,3,4,5,6-pentasubstituted pyridines at room temperature. Atom economy, excellent yields and mild reaction conditions are some of the important features of this protocol.
It may be useful for you.
Good luck
you have got probably polymerized material.it has not gone to desired reaction,it is self polymezation of aldehyde
As the product not soluble in DCM, dioxane, benzene, THF, Acetic Acid, MeOH, ETOH, DMSO, DMF,ETOAc and or/ Hexane, it may be a polymer.
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