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Topic: Nitration Of Indole  (Read 7784 times)

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Offline rameshsbdu

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Nitration Of Indole
« on: July 11, 2010, 02:18:51 AM »
How to synthesis 4-amino-,1,2,3-trimethylindole, and 5-amino-1,2,3-trimetylindole and is there possibility of conversion from 5-amino to 4-aminoindole in one step or two steps

Offline SVXX

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Re: Nitration Of Indole
« Reply #1 on: July 11, 2010, 02:45:26 AM »
The most electron rich position of indole is the second carbon or third position, following usual nomenclature(the one not in the benzene ring). As per Wiki, that position is 1013 times more reactive than the whole of benzene. If you want to nitrate indole, the reaction will almost exclusively leave a nitro group at the third position. You'll need some way to get around that.
The proton attached to nitrogen of indole is acidic(first position), and so are the protons attached to carbons of the second and third positions. So you can easily deprotonate them with a base and do a nucleophilic substitution using them as nucleophiles, turn by turn, on methyl halides or CH3-X (X = Cl, Br, I). So getting the 1,2,3-trimethyl part is fairly easy. Infact nucleophilic substitution cannot occur anywhere else in indole if the 1,2,3 positions are not already taken.
For the 4 and 5 amino parts, like I said, you'll have to use the concepts of electrophilic aromatic substitution, and place suitable electron withdrawing or releasing groups(which are easily removable once the job is done) to direct your nitro group.
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Offline sjb

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Re: Nitration Of Indole
« Reply #2 on: July 11, 2010, 06:42:05 AM »
Nitration, or amination? Your subject and text don't match, so it is unclear what you are enquiring about.

If you have a suitably protected indole (and 1,2,3-trimethyl I think is such a beast), could you go via a benzyne intermediate to convert 5-amino to 4-amino? Otherwise, there's a prep for 4-nitroindole at http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0493, but can't see this being easily amenable to the 1,2,3-trisubstituted compound.

Offline rameshsbdu

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Re: Nitration Of Indole
« Reply #3 on: July 12, 2010, 02:41:05 AM »
thank you for your suggestion, but i have some different problem, that also i promoted can you tell me the possible answer?

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