dennis_pro (HyperLab Bee)
07-22-02 16:39
No 335952
       Indomethacin oxidizing?  Bookmark   

a) 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid (indomethacin) + KMnO4 (or other oxydizer) -> 1-(p-chlorobenzoyl)-5-methoxy-2-carboxy-3-acetic acid
b) 1-(p-chlorobenzoyl)-5-methoxy-2-carboxy-indolyl-3-acetic acid + H2SO4 -> 5-methoxy-indolyl-3-acetic acid
c) 5-methoxy-indolyl-3-acetic acid + SOCl2 -> 5-methoxy-indolyl-3-acetic acid chloroanhydride
d) 5-methoxy-indolyl-3-acetic acid chloroanhydride + NHMe2 -> 5-methoxy-indolyl-3-acetic acid N,N-dimethylamide
e) 5-methoxy-indolyl-3-acetic acid N,N-dimethylamide + LiAlH4 -> 5-MeO-DMT

Is it possible? wink Especially first study? Or indole ring will crashed?
With best regards,
Dennis Prochko aka Wolf 		 
 
 
 
    Rhodium
(Chief Bee)
07-22-02 17:21
No 335968
       I have seen in Tihkal that Indomethacin is a ...  Bookmark   

I have seen in Tihkal that Indomethacin is a precursor to 2,5,N,N-Tetramethylserotonin... 		 
 
 
 
    dennis_pro
(HyperLab Bee)
07-22-02 17:33
No 335972
       Yes, but...  Bookmark   

I have readed TIHKAL.
Entry #45 (5-MEO-TMT) produced from indomethacin is not so sweet as 5-MeO-DMT frown.
Shulgin wrote: "This exact same chemical, if you were to remove that tiny, little, bitty methyl group at the indolic 2-position, would become the remarkably potent material 5-MeO-DMT.". And my question is: can I "remove that tiny, little, bitty methyl group" with KMnO4 and further decarboxylation? Or indole ring in indomethacin will be crushed with KMnO4?
With best regards,
Dennis Prochko aka Wolf 		 
 
 
 
    Rhodium
(Chief Bee)
07-22-02 18:59
No 335995
       I believe he did not mean "remove" in the literal ...  Bookmark   

I believe he did not mean "remove" in the literal sense, rather that if the molecule was to have been built without that group in the first place.