Author Topic: Indomethacin oxidizing?  (Read 1593 times)

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dennis_pro

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Indomethacin oxidizing?
« on: July 22, 2002, 04:39:00 PM »
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?  ;)  Especially first study? Or indole ring will crashed?

With best regards,
Dennis Prochko aka Wolf

Rhodium

  • Guest
I have seen in Tihkal that Indomethacin is a ...
« Reply #1 on: July 22, 2002, 05:21:00 PM »
I have seen in Tihkal that Indomethacin is a precursor to 2,5,N,N-Tetramethylserotonin...

dennis_pro

  • Guest
Yes, but...
« Reply #2 on: July 22, 2002, 05:33:00 PM »
I have readed TIHKAL.
Entry #45 (5-MEO-TMT) produced from indomethacin is not so sweet as 5-MeO-DMT  :( .
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

  • Guest
I believe he did not mean "remove" in the literal ...
« Reply #3 on: July 22, 2002, 06:59:00 PM »
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.