o-toluidine

[Cheapskate]

Yes, I'm still on the quaalude thing!

I heard of someone who was trying to simplify the synthesis of o-toluidine by a reduction of nitrotoluene with zinc and NaOH.  This produced a deep red result that after filtering and treating with HCl held at a reflux for a while yielded o-tolidine.  Damn, so close!

Now the question is tolidine is two toluidines hooked together, can this bond be broken and give the target??  If not, this person has some great red dye for his shirts.

[Cheapskate]

Believe it or not, I worked with the aspirin idea a couple of years ago and never got it to work.  I believe it can be made to work, but at that time I didn't have the skills or stuff to really attack it correctly. 

Even if one were to conquer easily made anthranillic acid, one still has the problem of o-toluidine to conquer and you and I both hate the iron reduction and it didn't seem like the tin one was any better.  Zinc is pretty nasty also, and I haven't completed working it up yet.  But I stumbled over the tolidine thing and this just looks too promising.

Now, how does one break a carbon to carbon bond between two rings??

[psyloxy]

"HBR should replace the OH with BR..."
No way !

--psyloxy--

[FILO]

What if you reacted O-Tolidine with Acetylanthrinilic Acid ? you would have 2 Qualude Molecules back to back:) It may be a super lude.

[blanka]

If only if superluud were so easy to make

[Krypto]

Looked up O-toluidine in an old chem book and the method of derivation given is,
Reduction of ortho-nitrotoluene or obtained mixed with para-toluidine by the reduction of crude nitrotoluene.

Hope it helps some, doesn't say anything about tolidine, but I'll do some more looking.

Kr

[Cheapskate]

Does it give a reduction method other than dissolving iron or tin?  These have both been tried and are really messy.  We're looking for something that doesn't stink real bad and doesn't have to be steam distilled.  If you heat up nitrotoluene it will smell up the entire neighborhood.  It is also incredibly hard to clean up after.

[lugh]

The Electrolytic Preparation of Anthranillic Acid
Canadian Journal of Research
Vol 13, Sec B
September 1935, No 3, pp 123-32
Shipley and Calhoun

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