Hi,

SWIM was trying to produce butaqualone...yes, a new compound!
SWIM was using isatoic anhydride and ortho-butylaniline. The procedure SWIM is following is below;
(ortho-butylaniline instead of o-toluidine)

"A mixture of 8g isatoic anhydride and 5.5g o-toluidine in toluene (500-750 ml) is refluxed for two hours. Acetylacetone (2.5g) containing a few ml of concentrated hydrochloric acid (to form the hydrochloride) is then added, and refluxing is continued for another hour. Evaporation of the solvent gives methaqualone hydrochloride, which is purified by recrystallization from hot methanol. The yield is 80%."

The reaction didn't seems to work out, even when SWIM did a test run a year back to make methaqualone. SWIM got a crystalline precipitate right after adding the HCl and SWIM assumes it's o-toluidine HCl?. (SWIM got a final product after evaporation that didn't hit the correct melting point after recrystallization too.) SWIM is not sure what SWIM produced...
Would you recommend reacting the acetylacetone for an hour and then add the HCl, or is the HCl working as a catalyst too?

Has anyone done this reaction before to share some insight?  Or Does anyone have this file below? It would be helpful.
Manhas, A Facile Synthesis of Methaqualone and Analogs, Synthesis 5, 309-10 (1977)


thank you!

I didn't simply swap the o-butylaniline for the o-toluidine based on the same weight of the original substance. I adjusted the amount of o-butylaniline based on stoichiometric calculations and did write out the reaction before hand to show the workings of it.
I was just asking if anyone had any experience with this reaction and what they might have done differently. I also asked a couple questions in my first post that I think were legitimate questions. Enlighten me if you would have asked in a different manner.

Hi Stinky1,

First off let me make it clear I am not trying to blatantly be a dick to you, and I do not think you are of any less worth than anyone here.

I assumed you would fix the stoichiometry, but it still seemed as if you just wanted to swap this reagent to get the butyl analogue and be done with it, with the statement about how you tested the reaction for methaqualone.
You did ask legitimate questions, but generally if someone is to come and ask for information and write a post full of SWIM and not much more information really, it won't be beneficial for you.
Therefore I propose you include just more information about what happened, so far I know something precipitated. Color, exotherm, all of that. It may not even help to get an answer if you state all this, but it sure does show you put more effort and care into it and trust me people appreciate this.

One pot methods sure are nice but maybe you can try condensing the anhydride with your aniline directly instead, since I don't know if anything about this particular substance is available you probably don't have much info to go off of. Use TLC if possible, see if you get a new product. I would say if you get some material from this, go on and try the next part with acetylacetone. Honestly if it is completely new, you need to take NMR of it and see if you have what you want. And that means making a friend, paying someone, etc. who does have access to the instrument.
It's going to take experimentation, that's the extent of my advice since I have not attempted this method for making that class of compounds.

Good luck

^+1

I will provide more information next time, but I need to learn to keep better notes on details of the reaction. I should also invest in a FT-IR since the older ones seem relatively inexpensive. Although gaining access to an NMR would be very helpful.

Thanks for all the replies and i really appreciate the file. I have been looking for this for a long time. I definitely need to learn how to get these documents that are usually locked in those institutional websites.

“..you are of any less worth than anyone here. “ This is all I ask for, thank you. It seems hard to come by as on other forums people usually jump on the opportunity to put people down.

About the melting point of the”butaqualone Hcl”, I didn't have any literature value to compare to, but it should have been around the melting point of methaqualone hcl or higher, as etaqualone Hcl has a melting point higher then that of methaqualone Hcl (ethaqualone hcl mp:~247C). From the methaqualone reaction i did, the sample i got at the end had a melting point of 185-190C after recrystallization. It was supposed to be about 235-237°C.
If it was still contaminated with something else, although looking pure, I guess that would cause the melting point to be lower.

I also need to remember to use TLC, I keep forgetting about this method.
I thought I would try the reaction with the o-butylaniline just because I was generally experimenting. I was just hoping for a good outcome, but maybe I didn't react long enough or didn't use enough toluene (450mL). The more I am thinking about this maybe that is the cause of the precipitate.
----------------
 “there shouldn't be enough o-toluidine left to crystallize. Maybe your isatoic anhydride was exposed to water, and has degraded.”

What would the isatoic anhydride turn into if it comes into contact with moisture? isatoic acid?
I probably should check the melting point of this compound as It has been sitting around...
If it degraded then what you stated sounds like what happened...the o-toluidine Hcl precipitated.
More crystals did form after it cooled too, and I should have added a base to see if it turned into a liquid as methaqualone base is still a solid...oh well
As you can tell I am not the most experienced chemist lol
Maybe I should try this reaction again and get back to you all in this forum...& maybe with some pictures from start to finish.

Just start slowly, as with any unknown compound, or little known one. Methyl-methaqualone is a convulsant, or it certainly appears to be. And if Toady recalls his toxicology education correctly, overdoses of methaqualone itself cause convulsions, which is paradoxical with a GABAa agonist (or allosteric modulator, he should say, strictly speaking)

He seems to recall something about the methylated methaqualone derivative circulating on the research chemical market some time ago, and causing seizures, and in lower doses, gross motor tremors and twitching of the extremities. There appeared, batch differences aside, to be a VERY wide range of doses this occurred at. Some people were doing a few milligrams IIRC on bluelight, and finding that it was causing blackouts and clonus. Others didn't see this effect until they started bong-hitting hundreds of milligrams. Others didn't see it at all and loved the stuff.

Just be careful, although this isn't an alkyl ring-substituted derivative like MMQ.



 MMQ Toady recalls as possibly being an AMPA receptor agonist, which is BAD NEWS. Would explain memory blackouts and seizure (ala domoic acid...excitotoxic damage can be permanent)