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Author: Subject: anthranilic acid
Albertson
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shocked.gif posted on 2-8-2016 at 10:05
anthranilic acid


So i was synthesizing Anthranilic acid. Everything had been done according to https://www.erowid.org/archive/rhodium/chemistry/anthranilic... Yet when i was adding GAA bubbling did occure and co2 had been given off but after adding 20 mls as told nothing precipitated.Solution remained brownish orange color. So are there any ideas what happened and how to get the acid out ? Thanks.
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Metacelsus
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[*] posted on 2-8-2016 at 16:22


Remove two small aliquots of the solution. To one, slowly add acid. To the other, slowly add base. Watch for precipitation.
If nothing precipiates from either, you're out of luck. As a last-ditch effort, add copper sulfate to precipitate copper anthranilate.

I tried that Erowid procedure a few years ago, and it gave very poor yields. Chemplayer's is better. Also, I've been able to consistently use hydrochloric acid for the final neutralization by testing the amount needed on a small aliquot of solution (basically, doing a titration). Hydrochloric acid is significantly cheaper than glacial acetic acid (for me).




As below, so above.

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Albertson
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[*] posted on 2-8-2016 at 16:45


I've tried chemplayers method yet i still got the same problem so i guess the problem is in reagents though fumes were given off when heated with bleach(i suppose that indicates rearrangement). i've made a new batch of phthalimide yet it requires recrystallisation.
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DailyInsanity
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[*] posted on 29-9-2016 at 04:28


I've tried both methods, Chemplayers method a couple of times, and I have also experienced similar problems. Even after adding some copper sulfate and working up the copper anthranilate I don't seem to get any product.

I really can't explain this because everything before hand seems to indicate the reaction is proceeding correctly, and it seems like many people are having this problem. Soon I'm going to try the reaction again, but with freshly prepared hypochlorite solution and see how it goes.
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