which solvent you are using for?? and what about the temperature?? perhaps the media is very acid. Despite the molecules are very bulky, I would recomend no acid media or another acid such as mCPBA
Imines with aromatic amine are quite unstable compared to aliphatic system. That is why aniline is used as catalyst, as it forms imine quickly, which can be displaced by other reactive amine Try using triflic acid as catalyst
about your question, both ur amine and aldehyde are aromatic and this can be easily formed a schiff base ,but is your amine consider as a neucleophile ? check the pKb ? I think the the lone pair of NH2 is busy with aromatic system by conjugation with carbonyl of anthraquinone ..u can use dean stark process to condensation of ur reaction , with check TLC .
Both of your reagents are so bulky, hence due to steric hindrance, may be you are not getting Schiff-base from them. Use of mild acid is ok, but I think strong dehydrating agent is also required for this condensation.
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