Synthesizing 2,6-xylidine from nitromesitylene in a lab

[JeffEvarts]

Lab production of 2,6-Xylidine appears to be difficult. Apparently either the production or reduction of 1,6-dimethyl nitrobenzene is "hard". Industrial production involves 50+ atmospheres of pressure, which falls far outside of my definition of "lab production".

I'm interested in taking a third approach: start with nitromesitylene.

Strategy 1: Somehow, magically, remove the methyl group that is para to the nitro group, then reduce the nitro group to an amine.
Strategy 2: Reverse the steps above: Reduce, then demethylate the aminomesitylene

My questions for all you "real" chemists out there:

1. How do I remove the correct methyl group from nitromesitylene?
2. What challenges do I face in reducing it to an amine? Reducing 4-nitrotoluene acid to 4-aminotoluene isn't too difficult, I hear. I assume the additional methyl groups are the cause of any difficulty?

Thank you in advance - Any help or pointers gratefully accepted
-Jeff Evarts

 

[DrClaude]

As this molecule is a precursor to lidocaine, we prefer not discussing its synthesis on PhysicsForums.

For more details, our guidelines concerning chemical activities can be found here.

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