I would suggest reduction of the nitro group using tin chloride. This method worked fine in my hands, not for this particular reaction involving crown ether but in general. Actually, I never worked with crown ether, but I would assume, that you could seperate the product from the nitro compound by column chromatography. There should be differences in the retention, since the nitro group is more lipophilic compared to the aromatic amine.
Thank you very much Mr. Daniel Ramsbeck.
Generally, for amination of nitro group, Sn/HCl can be used. Actually, In literature, i did not found any article using this reagent for amination of nitrobenzo crown ether. Shchori et. al. have used Pd/C, hydrazine in 2-methoxy ethanol ( Journal of the American Chemical Society / 95:12 / June 13, 1973) and thereafter many places it has been used in this purpose. Is there any role of etheric oxygen groups of crown ether for selecting the amination agent?
Actually, I cannot really answer the question concerning the role of the ether oxygen. As already mentioned, I´m not familiar with crown ether. But maybe they could form a complex with metal in the reduction and therefore metals have not been used for such reductions. Anyway, I would give it a try! I would use tin(II) chloride, maybe EtOH as solvent. Not Sn/HCl.
Sn likes to coordinate with ligands. Oxygen in ether might go after the Sn making the reaction slow. I would give a try and check the % yield.
Thanks Chammi Palehepitiya Gamage. Looking forward to see the yield.
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