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Author: Subject: Methods of synthesizing 2‐aminobenzonitrile?
Hockeydemon
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[*] posted on 31-8-2016 at 16:47
Methods of synthesizing 2‐aminobenzonitrile?


I recently found some publications that use 2-aminobenzonitrile in microwave assisted chemistry to form quinazolines. Theoretically, are there reasonable methods for a hobbyist to synthesize 2-aminobenzonitrile?

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Cryolite.
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[*] posted on 31-8-2016 at 17:50


The obvious route would be to start from anthranilic acid (made by hoffman degradation of phtalimide), esterify it to methanol (methyl anthranilate), perform ammoniolysis with aqueous ammonia to form the amide, and finally dehydrate with phosphorus pentoxide to the nitrile. However, this seems like a lot of work....

However, why would you bother? The classical preparations of methaqualone utilize the plain acid with acetic anhydride or polyphosphoric acid as drying agents, and get good enough yields. I believe that this method of ring formation would work just as well with a more complicated quinazoline system, unless you are working with something really exotic.

I do recall a method of synthesizing aromatic nitriles from the corresponding acid using excess urea and stoichiometric sulfamic acid, but I do not recall the patent number at the moment.
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