[darkdevil]

Hi,
I wonder if i can make this compound from 1,4-diaminobenzene?

1,4-diaminobenzene ---NBS---> dibromo-1,4-diaminobenzene ---suzuki coupling--> product?


Or are there any better ways to do so?

[darkdevil]

Oh no..
 I added 2  eqv. of NBS (catalyzed by NH4OAc in MeCN according to a paper of brominating aniline)to 1,4-diaminobenzene and the whole thing turned black immediately. Cannot obtain anyting

[darkdevil]

Do you think I can do a Hofmann–Martius rearrangement? by first alkylate the N atom on 1,4-diaminobenzene???

http://en.wikipedia.org/wiki/Hofmann%E2%80%93Martius_rearrangement

[Babcock_Hall]

Your first attachment is not showing up correctly.

[darkdevil]

Can you see now?

[Babcock_Hall]

It is showing up now.  There are others here with more synthetic experience than I have, especially with respect to aromatic rings.  However, I am curious whether or not you have considered and ruled out strategies involving Friedel-Krafts alkylations or acylations.  I could envision that it would take several steps.

[discodermolide]

Do you think I can do a Hofmann–Martius rearrangement? by first alkylate the N atom on 1,4-diaminobenzene???

http://en.wikipedia.org/wiki/Hofmann%E2%80%93Martius_rearrangement

If you try this with your 7 carbon chain alkylation will provide a mixture of mono and di-alkylated products. The best way to get a mono-alkyl product is reductive amination so you will need the aldehyde corresponding to your chain.
It may be better to start with 4-nitro aniline if it's available, work on the first amino group, then reduce the nitro to amine and repeat. That way you may get less side products?.

[darkdevil]

I have some 4-nitroaniline that I might try to use them as starting material.
What I want to do is to add some alky chain(s) to the aroatic ring of the 1,4-diaminobenzene
Can I directly do Friedel Craft alkylation on 4-nitroaniline ?  And then reduce the nitro group to amine to get my product?

[discodermolide]

No the ring is probably too deactivated.
Try the reaction you mentioned above.

[darkdevil]

Do you mean I shall perform Hofmann–Martius rearrangement on an N-alkylated 4-nitroaniline ?

[orgopete]

Is this a question about obtaining the product or a question for an ochem class? If it is an ochem question, I suggest beginning with the most recent chemistry in class and/or your book.

[discodermolide]

Do you mean I shall perform Hofmann–Martius rearrangement on an N-alkylated 4-nitroaniline ?

Yes, that's what I mean

[Babcock_Hall]

Would it be possible to acetylate the two amino groups, then add the two alkyl groups, then deacetylate? 

[mst]

Just make the corresponding amide or imine and reduce it.

[Babcock_Hall]

1,4-diacetamidobenzene is a known compound.  The question is whether one can control the number and regiochemistry of alkyl or acyl groups that one would add to it.  The removal of the acetyl groups could be done with 6 M HCl at elevated temperature.  I don't have anything against disco's route; I am just thinking out loud.