Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: jmart14 on January 17, 2014, 02:46:03 PM
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So my desired product is ortho phenylenediamine with a sulfate/sulfonic acid group that is para to one amide group and meta to the other. Suggestions? Not neccessarily any specific starting materials.
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A few, though in the interest of keeping with the forum rules how about you start by telling us some of your ideas?
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I am attempting to synthesis benzene with the ortho amines with the sulfo groups on the opposite side to increase water solubility. Once made it will be reacted through a condensation reaction will phendione (1,10-phenanthroline-5,6-dione) to form a dppz (dipyridophenazine) ligand that has the the sulfo group on the opposite end of the phenanthroline. Thus far my attempts were reacting 2-nitro-5-chloroaniline with dimethylamine in DMF with potassium carbonate, NMR resulted in an unexpected spectra, indicating side reactions. However ei-ms indicated the correct product. Upon reduction attempts of the product (desired 2-nitro-5-dimethylaniline) apparently the reaction is extremely air sensitive.
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@ the unassuming, didnt see the rules initially, thanks for the heads up.
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No worries!
Looking around a little bit I was able to find this paper: Tetrahedron Volume 64, Issue 22, 26 May 2008, Pages 5410–5415. Where they take o-phenylenediamine and cook it at 137C in conc. sulfuric acid to give the product directly in 96% yield! This would be a much faster and direct method to your desired material.
Give it a try and let us know how it works out for you!
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Will do, thanks looks useful.