DraconicAcid
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Registered: 1-2-2013
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Anthranilate Oxidation
We all know that anthranilates are easily oxidized to dark-coloured crud.
I'd like to oxidize methyl anthranilate to methyl 2-nitrobenzoate.
I've read through this review about the oxidation of anilines to nitroarenes.
https://www.mdpi.com/2624-8549/4/1/7/htm#:~:text=Oxidation%2...
I don't have the fancy stuff like oxone(TM) or acetonitrile (let along the phosphotungstate catalysts mentioned), but the peroxide oxidations seem
feasible. Anyone have experience with this?
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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Boffis
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Hi DraconicAcid, I don't know much about the oxidation of amines to nitro compounds I think you are probably going to struggle with this route. Have
you checked out the Sandmayer type reaction via the diazonium salt of methyl anthranilate and either excess nitrite or with one of the
nitritometallate complexes? I recently came across some preparations in an old book on Naphthalene chemistry of obscure nitronaphathalenes via this
reaction. Sodium cobaltinitrite was used as the source of nitrite ions in some cases while sodium nitrite was used in others. Cuprous oxide was used
as a catalyst in some case. It seemed to have fairly general utility for naphthalene derivatives and given that anthranilate ester should be soluble
in cold dilute mineral acid I think this should be worth a shot.
I will see if I can dig up some references.
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