IAA methyl ester ?

[Noid]

Is it the same as 3-Indoleacetic Acid?

@

https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleaceticacid.html

there is a [Note: The actual reagent is IAA methyl ester, not the free acid]

So how do you tell the difference? This chemical appears to be widely available, yet commonly reffered to as 3-Indoleacetic Acid, im wondering if it's the right stuff. 60g @ 150.oous sounds about right? This chem is otc I presume as it's used as plant growth factor or something alike.

This synth  converts this acid into the amine, and it is said there is 2 ways to do this, direct transformation using glycol as a solvent, or 40% aqueous dimethylamine, sol and H2SO4 as a catalyst.

Why did this person follow the later? Wouldn't a direct transformation of the acid gave a higher yeild and be easier? I am just assuming that the the previous would be easier, can someone elaborate on the direct transformation process? 40% diethlamine is a tough one to find, unless it's sold under under a different name, which is probably the case.

Also As with ALL hydride reductions, an overhead mechanical stirrer is very much preferred over a magnetic stirrer. It just works better.

Would this be the case on scaled down rxns calling for 5-10g LiAlH4??

Tootie

[Rhodium]

I added that note, as it is obvious from reading the detailed procedures at the bottom of the doc that the Indole-Acetic Acid (IAA) of commerce must first be converted to its methyl ester before it can be further reacted with dimethylamine. The author of the section at the top forgot to mention that. Myself, I do not think that a direct conversion of IAA to the amide is going to work especially good, and also, that author is erroneously quoting Fish as starting with the free acid, while he actually starts with the methyl ester of the IAA.

Yes, good magnetic stirring is adequate for 5-10g LAH reductions.

[Noid]

Ok, so basically a step has been left out in the above overview? The conversion or IAA acid -> IAA methyl ester should be the first step, then the ester to the amine via 40% aqueous solution of dimethylamine and H2SO4 etc.. ?

Would the correct change in this error look like this?

In the first step the acid is converted to the amine,
In the first step the acid is made to the ester, then ester, to the amine?

Is this a practical synth for a first time DMT dream? 

Thanx  

[Rhodium]

I have no idea what the H₂SO₄ would be good for. Just follow the illustrated synthesis at the bottom of the doc, which shows the correct sequence: Acid -> Ester -> Amide -> Amine

[Noid]

Thanx Rhodium.

[Noid]

Is Indole-3-acetic acid going to the same chem as 3-Indoleacetic Acid

It's the placement of the 3 that is throwing me off. If it is, why is it ok to put the "3" wherever?

[Rhodium]

They are the same compound, and if being very precise, it is not proper to put the "3" just anywhere. it has to do with how old the naming convention is - in different times people liked to name compounds in different ways (and it is best to know all the possible ways) - think of it, regardless of where the "3" is placed, you can't arrange the atoms in another fashion than a standard indole nucleus, with a -CH₂COOH sticking out in the 3-position (which is the carbon on the small pyrrole ring which isn't next to the nitrogen).

The current IUPAC nomenclature is even worse, they actually want us to name IAA something as hideous as (1H-Indol-3-yl)-acetic acid!

[hypo]

the germans traditionally put the number in front: 1-bromo-2-propanol
the french traditionally put it behind: bromo-1-propanol-2
iupac puts numbers directly in front of the function: 1-bromo-propan-2-ol

sidenote: when schools in the rest of the world were changing from
german nomenclature to iupac, french schools changed from french to
german nomenclature. chaos.  

[Noid]

I have one last set of questions for a while, for I plan on taking some time to learn more about the TLC process, as I don't quiet get the whole jist.

In the first section, as the acid forms the ester, this is verified with "TLC on alumina plates"

In the next section: the reaction was tested by TLC Silicagel/ethylacetate, Rf (amide) 0.5; Rf (ester) 0.8. The excess of DMA was evaporated at 20°C under reduced pressure to avoid hydrolysis. The product was filtered and purified by sublimation under diminished pressure to give 0.8 g (4 mmol, 80%), mp 119-120°C.

What kind of TLC plate was used in this manner? Why is the silica gel being introduced? When they reffer to the "eleunt" is this the same as ethylacetate in this example??

Can somebee break this down for me?

[LaBTop]

It's all thoroughly explained in numerous other threads, and there is such a wealth of info to get by just typing in the right words in a Google websearch or our Search Engine, that it's now time you start READING.

UTFSE, Google and a University library if possible.
And read the "How to - Use The Fuckin Search Engine - " sticky thread up there.

This goes for all you lazy newbees, earn your Membership of this community by proofing to us you'r cut from the right wood :

Inventive, self-supporting/supplying, thorough, dedicated, hardworking and selfstudying, but above all, NON-GREEDY at all times. LT/

[Noid]

Your right, but just so you know, I spent over 12 hours trying to learn about TLC yesterday, and not having ever done it makes it very confusing. I'll spend another 12 hours today, and then another 12 the next. I WILL accomplish my goal one way or another.

Thanks for the help that has been provided thus far. Back to TFSE..