Author Topic: Indole-3-acetaldehyde  (Read 1610 times)

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element109

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Indole-3-acetaldehyde
« on: May 29, 2000, 11:49:00 AM »
In the tryp/NaOCl synth, is it really necessary to use 700ml of benzene ?? And then evaporate it to 65 ml, when only containing 3-4 gr of material ??

Could any other oxidation agent be used, or oxidize it directly to the acetic acid (maybe KMnO4)

Any possible ways of reduction here ? Earlier posts (a year ago) suggest a leukart with DMF, but i don't know.

Could an amalgam with dimethylamine be used here ?


E109-

phaidon

  • Guest
Re: Indole-3-acetaldehyde
« Reply #1 on: May 30, 2000, 01:45:00 AM »
element109:

I-3-AcCHO could be used in a LW rxn to form dialkyltryptamines but as far as I know it has not
been tried. You might want to take a look at the tryptophol -> DMT synth somwhere around here
or at Rhodium's.

See, the objective in the Streccker degradation is to prevent the aldehyde from being brought into
contact with ANYthing it could react with. 700 ml of benzene should provide an adequate degree
of protection.

Oxidise? I-3-AcCHO to IAA? That's aldehyde to carboxylic acid, you would really want clean
I-3-AcCHO to start on that one. But then again, IAA isn't too expensive so you should pay
some thought to the amount of funds involved when doing:

1) Tryptophan -> I-3-AcCHO -> IAA
2) buying IAA

Hope it helps.

Laters,

-- phaidon, son of apollon

I scorched the Earth, now what do I do tomorrow?

element109

  • Guest
Re: Indole-3-acetaldehyde
« Reply #2 on: May 30, 2000, 06:25:00 PM »
I know about the leukart-wallach, i was just wondering if there are other ways of reducing it.

700ml benzene is a LOT to evaporate for 3-4 gr of aldehyde !

What would happen if SWIM used a stronger oxidation agent ?
First the 3-acetaldehyde is formed, which would to my crappy knowledge further oxidize into the 3-acetic acid ?
  -CHO --> -COOH

He has a vial of 50gr L-tryptophan and wants to do something with it. It really cheap and EZ to get here.
It would be neat to find a high yielding way of tryp --> IAA, when the dark days come when IAA will not be easily available then there's always that.

The tryptophol way is sure interesting but it's a multistep way.


For curiosity i'm going to dig up the following ref.:

   DEAKIN, H.D.,  Biochem.J. 12,319 (1916)

It talks about the oxidation of a-amino acids to aldehydes and nitriles using various reagents.


E109-

psyloxy

  • Guest
Re: Indole-3-acetaldehyde
« Reply #3 on: May 30, 2000, 08:18:00 PM »
The trp --> DMT synth is only a 2 Step one.

Trp --> tryptophol via yeast

Tryptophol --> DMT with Ni-catalyst and HN(CH3)2

You could also buy the tryptophol, for the potential it has in it, it's really cheap.

--psyloxy--


psyloxy

  • Guest
Re: Indole-3-acetaldehyde
« Reply #4 on: May 31, 2000, 02:01:00 PM »
Yes, it is a one step synth from tryptophol.
Trp is for tryptophan like gly is for glycine and ala for alanine ...

You can buy tryptophol without trouble and it really isn't that expensive
(search with chemfinder or ask SA or whatever) .

If you don't trust russian chemistry and/or want to be on the safe side,
it will be a 2 step synth: tryptophol --> indole-3-ethyl-Br with PBr3
(check out the refs from the other threads) But it should work with ZnBr2/HBr
too, maybe with somewhat reduced yield.

the I3EtBr --> DMT rxn is also not much of a problem, again, check out the refs.

--psyloxy--