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Author: Subject: Anthranilic acid fail
Metacelsus
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[*] posted on 16-7-2019 at 09:40


Salts, for example. Also oligomerized oxidation products (similar to aniline).

I agree that it probably isn't worth trying to purify the brown powder to get rid of the color. It could be 99.9% pure and still be brown. The brown stuff is probably good enough for most purposes.




As below, so above.

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Pumukli
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[*] posted on 17-7-2019 at 11:37


Thanks Amos, good to know that "cocoa powder" from this reaction is still as good as the original thing! :)

If you have some pure anthranilic acid - and some time - then you may conduct a precipitation experiment with it. I'd like to hear about the results of this. :)
Basically, dissolve some AA in dilute acetic acid and mix this solution with the solution of some water soluble Ca2+-salt. (Chloride, acetate, what you have at hand). Then wait and report what happens! I think you will got precipitation after a few hours (days), and that precipitate won't melt below 300 C.

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[*] posted on 21-7-2019 at 09:50


I slowly explore parts of this particular Hofmann rearrangement and I found it more and more interesting from an amateur's point of view.
A seemingly simple reaction but there are several stages and hidden steps involved and it is a challenge to try to trace them.

My biggest achievement is that I think I solved the "black tar" problem and now I know how to avoid it altogether!
I also prepared a few hundred milligrams pretty good AA at last (mp: 146-147 C). Yield is not great yet but hopefully I could improve it too.
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