LHcheM
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Registered: 20-2-2011
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Obtaining Anthanilic acid from Methyl Red
I have a great amount of methyl red which I find useless for indicator purposes only, so recently I cleaved the Diazo bond with zinc in 50% sulphuric
acid, zinc granules are used as I don't have powder. The reaction took 2 days to go to completion. During the time, the very deep red solution
gradually fades to colorless, and now a clear solution is obtained
Now the problem came: How can I separate the two products and isolate them?? I suppose the only products are anthranilic acid and
N,N-Dimethyl-p-aminoaniline right? But as I neutralize the acid I don't get any precipitate (which the aniline should be insoluble) What's wrong with
my strategy /reaction??
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UnintentionalChaos
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Do you have a reference for this reductive cleavage of the azo bond? I suspect that you may have just made the hydrazine. Can you find two spots on a
TLC or only one?
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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LHcheM
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yes, from Organic Chemistry by Solomons and Graham...
it said that Zn or SnCl2 can perform the reductive cleavage
Unfortunately my TLC plates were expired so I need to wait for my orders to arrive, so I can't test that...
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