Another member asked me this question in a PM a while ago, but I seldom ever log on here to check this board.
He wanted to know about forming NAOT from o-toluidine and GAA. He thought I'd know something about acetylation. I suppose it might have had something to do with my nick name and my attempt at making acetic anhydride. (I don't really have a clue about the specific aspects regarding acetylation and never pursued making acetic anhydride)
He said that when he mixed lab grade o-toluidine and lab grade acetic acid that there was a modest generation of heat. He went on to say that after an extended reflux (4hrs) he encountered the same problems as Sky when trying to use GAA and OT to form NAOT. No crystals were present after crashing in cold water and they weren't there even after standing overnight. The aqueous is dark pink, and there's some small blobs of oil. He believes that it all turned into o-toluidine acetate.
A warning to Rhodium regarding Cheapskate's prep: so according to two other bees, refluxing acetic acid and o-toluidine may not form NAOT.
References given to me in his question:
Post 108883 (missing)
(Sky: "O-Toluidine or O-Tolidine HCL", Novel Discourse)
Post 108558 (missing)
(dormouse: "Still playing with methaqualone -Cheapskate", Novel Discourse)
https://www.thevespiary.org/rhodium/Rhodium/chemistry/quaalude.cheapskate.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/quaalude.cheapskate.html)
improving the bowel movements of cats & dogs everywhere...
J, Klosa (known from many articles written on Quaalude) published Patent US3197473 (http://l2.espacenet.com/dips/viewer?PN=US3197473&CY=gb&LG=en&DB=EPD)
which is a method which does not use any other acetylating agent than acetic acid. The reaction is performed in polyphosphoric acid though. The full patent text can be found in Post 398805 (missing)
(Aurelius: "US patent 3197473", General Discourse).
Send Cheapskate a PM about it, he stops by from time to time.