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?

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With best regards,
Dennis Prochko aka Wolf

I have seen in Tihkal that Indomethacin is a precursor to 2,5,N,N-Tetramethylserotonin...

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?

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With best regards,
Dennis Prochko aka Wolf

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.