Hey Cheapskate 3

[obituary]

Sorry about the new thread, can't seem to reply to the other posts in the other threads obit has started.  don't know why. oh well.

isatin - oxidation by CrO3--> isatoic anhydride (in itself can be helpful)
Isatin -direct oxidation via alkali/H2O2--> anthranilic acid
or isatoic anhydride <--equilibrium in H+ -> anthranilic acid


if obituary is remembering right, both isatoic anhydride and anthranilic acid can be used in quualude synthesis. 

the reference is the book: Heterocyclic Compounds by R.M. Acheson (copyright) 1960.

[foxy2]

What about the pathway you showed starting from tryptophan?

"tryptophan -(something)-> formyl kynurenine -(something else)-> kynurenine -(the-only-something-else-that-really-matters-to-us)->; Anthranilic acid"

Where does this overlap with the following???
"isatin - oxidation by CrO3--> isatoic anhydride (in itself can be helpful)
Isatin -direct oxidation via alkali/H2O2--> anthranilic acid
or isatoic anhydride <--equilibrium in H+ -> anthranilic acid"


Foxy Failing to see the picture here???
Professor I need it explained more simply!


Do Your Part To Win The War

[obituary]

all of this is in an effort to supply anthranilic acid more easily than the traditional o-nitrotoluene route.  the isatoic anhydride route supplies an additional positive by being a partial replacement for anthranilic acid in itself.  swim hasn't seen the information for the biochemical degradation of tryptophan to anthranilic acid.  was just suggesting it as another possibility.  maybe no one else likes this information like swim does, but none-the-less it's still viable, good information.  plus, for those that mess with synthesizing DMT and other tryptamines, this is a fairly good area of study.  swim is going to do some research and get some results on the isatin-> anthranilic acid by both routes to see yeilds, procedures, and ease of rxn for clandestine chemists. 

if there is something specific you would like to ask or don't grasp/understand, just post it, and if at all possible swim will answer.

[foxy2]

Yes a detailed write-up on how I can go from tryptophan-->anthranilic acid would be nice

   



Sorry i just got lost in the rather disconected posts under similar titles, i thought they were all working towards the same method.  I wish i had time to lit search however i barely have time to read the new hive posts.  There are so many things on my list of to do i just don't fucking know where to start.

Keep trying, some of us are interested.

If you could post all your references that would be cool.

Do Your Part To Win The War

[obituary]

The Tryptophan synthesis will have to wait  sorry. will look for some more refs for it though. 

will be doing the research on the isatin routes very soon. will post all details when finished.

[Cheapskate]

I found a reference on the web for the reaction from isatin to isatoic anhydride that you mentioned.  This actually looked relatively easy.  Haven't tried it (where the hell does one get isatin?).  But the darn method to quaaludes still need o-toluidine.  The path to o-toluidine is the problem.  I can make anthranilic easily with KMno4 and acetic acid and the o-toluidine.

I got a hint from the article posted in the meth forum about large scale meth production.  The author used a large stanless pot and a hand made condenser to reflux and distill gallons.  I actually tried this!  Stirring was with a surplus gear driven motor and the condenser I made was around 5 feet tall.  The whole contraption was 9 feet tall when set up and stirring on a hot plate.  Didn't stink much, but the distillation was a real pain.  Ever tried to keep a five foot condenser supported and on a hot plate that is setting on a table.

The distillation stunk to high heaven!  Did it on a rainy day with lots of wind to keep the locals from smelling it much.  I got about a liter of impure o-toluidine (I think) that I haven't distilled yet to see how pure it really was.  I can't repeat the procedure until the next major storm, so it may be a while.  I also can't get all the iron solids out of the pot.  It seems to have just melted into the stainless surface and won't even scrub out.

Don't misunderstand, I am very interested in any method to get the precursors to methaqualone.  I'm just so damn frustrated by o-toluidine.

[lugh]

The chromic acid oxidation of isatin to isatoic anhydride is referenced in J. Prakt. Chem., [2], 30, 84 (1884); carbon dioxide is lost during the acid hydrolysis into anthranilic acid. Akaline hydrogen peroxide oxidation of isatin directly yields anthranilic acid; JACS 54, 1917 (1932) & 63, 2027 (1941). Also, aniline can be converted into isatin, J. Prakt. Chem., [2] 105, 137 (1922).

[foxy2]

Thanks lugh

Do Your Part To Win The War

[obituary]

Well since this has all been done before, ....
try this new/old way to anthranilic a. and make a crap-load. take half- reduce acid to alkane-> you've got your o-toluidine right?  be sure to correct obit. if he's wrong.  just thought it looked easy enough.  smart/smart criticism not accepted/accepted.  have fun.

[lugh]

Some other references on the peroxide oxidation of anthanilic acid from isatin are: Berichte, 57, 2105 (1924); JACS 65, 1802 (1943); and HCA, 9, 578 (1926). Ortho-toluidine is generally made via the reduction of ortho-nitrotoluene, some references on that synthesis are: Proc. K. Acad. Wetensch 11, 248 (1908); Monatsh 31, 745 (1910); Rec. Trav. Chim. 33, 10 (1914); JCS 121, 270 (1922); CA 20, 389 (1926); Bull. Soc. Chim. Belg. 42, 80 (1933); JACS 65, 2426 (1943) & JCS 22, 112 (1944).