Author Topic: On not forming NAOT  (Read 4841 times)

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  • Guest
On not forming NAOT
« on: November 17, 2002, 09:44:00 AM »
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)

improving the bowel movements of cats & dogs everywhere...


  • Guest
Acetic only
« Reply #1 on: November 17, 2002, 10:58:00 AM »
J, Klosa (known from many articles written on Quaalude) published

Patent US3197473

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.


  • Guest
But not every single time.
« Reply #2 on: December 06, 2002, 10:37:00 AM »
I've done this exactly as MaDMax described above about 30 times.  I've had a few failures.

In the (maybe 5) times that failed the mother liquid just sat there and stared back at me and didn't form any crystals.  Never found out what went wrong.  In a few instances I tried some more reflux and more acid.  This worked once to create the crystals, but the other times....nada.

It worked perfectly the vast majority of the times.  I never, ever got the pretty white crystals that MaDMax did above.  They were always slightly pink.

Good job MaDMax!!


  • Guest
your fix!
« Reply #3 on: December 06, 2002, 02:22:00 PM »

If the rxn. fails to crystallize, adding a seed crystal from another batch will surely initiate crystallization of the desired product.  The amine was definitely acylated those times you experienced "failure", the product just failed to crystallize out.  Another way to isolate the N-Acetyl compound if crystallization fails is to simply evaporate off the excess acetic acid.  This will surely produce the desired solid product.


  • Guest
« Reply #4 on: December 07, 2002, 12:05:00 AM »
It turned out, as the bee in question PM'd me back, the problem was water in her acetic acid. She now refluxes for 5hrs and gets 60% yields. I sometimes wonder why she, herself, doesn't post that info in this thread.

Whatever. Take it easy guys, and a special thanks to madmax & his digital camera!

improving the bowel movements of cats & dogs everywhere...