Ormarion
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Making Phénazone from 4 amino phénazone
Hi everyone first post, im actually working on a project in organic chemistry wich would be to remove the tertiary amine of 4 aminophénazone to make
phénazone (i want to use it to make triboluminescent lanthanide complex).
If you are wondering why dont i directly buy phénazone, well i got 200g of this stuff for free and would like to use it for something instead of just
letting it cover in dust on a shelve
The procedure i actually found was to first transform this amine to an hydroxyle group using nitrous acid (from an old paper with a 92% yeild
apparently)
But then im kinda stuck after this, peoples have told me to use then tosyl chloride (wich i dont have but can make it from scrap) to remove the
hydroxyl but i would like to be as sure as possible before taking a week to make the tosyl chloride
If you have any suggestions of what to do with 4 amino phénazone too go for it, i already tried to complex it with lanthanum ( sort of yellow goo
glowing slightly under UV) and cerium (pink solution, no crystals or precipitate forming) and Uranium III (no real result).
(PS: im not english native so dont mind to much if i do some writting mistake)
[Edited on 31-7-2020 by Ormarion]
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Boffis
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By 4-aminophenazone are we talking amino-antipyrine (1-phenyl-2,3-dimethyl-4-amino-5-pyrazolone)? If so then can you not diazotize the amine group (it
readily forms diazonium salts) and apply reduction/degradation? I seem to recall that warming in alcohol or with hypophosphorus acid are the normal
procedures; this is a well established procedure. I can't remember the reaction name but I am sure there are examples in Vogel or similar organic
chemistry textbooks.
Alternatively prepare it from phenylhydrazine its an easy synthesis  .
diazotised amino-antipyrine couples with many phenolic compounds producing brightly coloured dyes, many of which act as metal ligands.
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Ormarion
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Aaah yea sorry i should have precise , its called 4-amino phénazone but its real formula is
4-(diméthylamino)-1,5-diméthyl-2-phényl-1,2-dihydro-3H-pyrazol-3-one , the amine have 2 methyl group on it.
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Ormarion
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In this case the reaction wont work, for the synth, well i need sodium to make the ethyl acetoacetate and more iodine than i already have for the
final reaction, that's why im searching an other way
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Boffis
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In that case I think you are pretty well stuffed. There is a reaction that removes dimethylamino groups in certain special occasions eg from
4-nitroso-N,N-dimethylaniline but I can't see it being much use in this case as there is no ring position left to substitute.
In the UK ethyl acetoacetate is still available from companies like APCpure, its noramlly the phenylhydrazine that is the problem; oh and the dimethyl
sulphate to convert the pyrazolone into antipyrine. Yes not exactly OTC!
I must admit that I just bought my antipyrine from a European ebay seller.
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Ormarion
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Well, im in France actually , i can buy 1l of ethyl acetoacetate for 35 euros, wich is more expensive than the liter of aniline i also got on this
site. for the dimethyl sulfate part ...i dont touch that kind of stuff. I should probably still try to see if the protocol i found to reduce it to an
hydroxyle group can make some nice complex.
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