[GregRC]

Hey guys, I'm new here, and I'm going to be doing some basic research this semester in synthesis. Thing is, it's been about 4 years since i've been in an O-chem class.



I'm still looking for my old textbook, so right now I'm not much help to myself.

[Dan]

I'm still looking for my old textbook, so right now I'm not much help to myself.

This is not a good excuse. Please read the Forum Rules - you must demonstrate some kind of attempt at a question before you will get much help, and forum policy is not to dump answers.

There is a wealth of information online about the reactions of aromatic amines that you can look at to get started. E.g.

http://www.chem.uky.edu/courses/che232/JEA/ln/3.%20Aromatic%20Chemistry.pdf
http://www.cliffsnotes.com/sciences/chemistry/organic-chemistry-ii/amines/reactions-of-amines

[kriggy]

Do you have any ideas how to proceed?
Try to look on each function group alone and think about how to convert it to the other

[GregRC]

What about the sandmeyer reaction?  NaNO2 and HCl.  Then CuCl?  Would that do anything to the primary amine? What about adding H2O after to get rid of the methyl?

[kriggy]

Yes, sadmayer should work. You cant actualy get rid of the -CH₃, you need that carbon. What about KMnO₄?

[GregRC]

Wouldn't that add 2 oxygens though?

[kriggy]

indeed. look at the function group it creates and then you can continue further. And btw, it could also react with another function group in your molecule

[GregRC]

So H2/Pd then?  Would i have to use a protecting group?

[kriggy]

Im not sure on H₂/Pd you would probably need something else.
I think you need to use protecting group im not sure which one. Its getting more interesting than I thought before lol

[GregRC]

Anyone have any thoughts on how to proceed with the methyl group?  Apparently this is my first project on Monday.

[discodermolide]

What does permanganate do to aromatic methyl groups? Which product is formed?

[AlphaScent]

Sandmeyer>Oxidize>??>??>product

This is where you are at.  Think about what discodermolide said.  Then go from there.

Sometimes you have to take two steps forward and then one back in o-chem...

[kriggy]

Sandmeyer>Oxidize>??>??>product

This is where you are at.  Think about what discodermolide said.  Then go from there.

I think you need to oxidize before sandmayer otherwise it could convert amino group into nitro.

Sometimes you have to take two steps forward and then one back in o-chem...

Exactly this. I cant say how much truth is in this sentence

[discodermolide]

The nitro group will not convert to an amine under oxidising conditions. Reduction of nitro groups provides amines.

[AlphaScent]

Sandmeyer is done to produce the halide.  In this case a chloride.  You have to do this first and then oxidize.  With a halide and nitro group present, the methyl would react to form an oxidized product.  Presumably an acid.