ORGLIST: Phenyl indole synthesis

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From: mohd zulkefeli (mzmj$##$hiroshima-u.ac.jp)
Date: Mon Sep 03 2001 - 07:00:39 EDT


Dear Members,

  I'm now working on synthesis of phenyl indole compound using m-Tolyl
hydrazine and 4-methyl acetophenon as a starting compound. From a few
references of indole synthesis (mostly by Fischer method) using ketone and
hydrazine, it was reported that a yellow crystal will be gained after
reacted those compounds with polyphosphoric acid or methane sulfonic acid or
zinc chloride as a catalyst.

  I have tried all these catalyst by reflux stirring of the ketone and
hydrazine in dist. MeOH or strring in r.t. with dichloro methane as solvent.
But the problem is, I never success to isolate the new product (determined
by TLC) as a cystal (which is always be an dark yellow oil) and what makes
me curious is even if I reacted the ketone with half equivalent of
hydrazine, the spot of ketone observed by TLC was never vanished.

   Does anybody know how to synthesis or ever do the syntesis of this phenyl
indole compound? I would like to know about the solvent used, the catalyst
and how to isolate it with a good yield.

   Thank you in advances.

Best regards,

M.Zulkefeli

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