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All 8 posts Subject: o-toluidine Please login to post Down

Cheapskate
(Stranger)
05-10-00 01:21
No 2118
      o-toluidine

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
(Stranger)
05-10-00 17:21
No 2443
      Re: o-toluidine

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
(Newbee)
05-10-00 17:57
No 2462
      Re: o-toluidine

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

--psyloxy--

FILO
(Stranger)
05-11-00 01:15
No 2615
      Re: o-toluidine

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
(Stranger)
05-12-00 08:35
No 3177
      Re: o-toluidine

If only if superluud were so easy to make :)

Krypto
(Stranger)
05-25-00 02:44
No 8976
      Re: o-toluidine

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
(Stranger)
05-26-00 16:49
No 9659
      Re: o-toluidine

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
(Moderator)
01-07-04 03:03
No 480845
      Electrolytic Anthranillic Acid
(Rated as: good read)

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

Chemistry is our Covalent Bond

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		Cheapskate (Stranger) 05-10-00 01:21 No 2118				o-toluidine
						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 (Stranger) 05-10-00 17:21 No 2443				Re: o-toluidine
						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 (Newbee) 05-10-00 17:57 No 2462				Re: o-toluidine
						"HBR should replace the OH with BR..." No way ! --psyloxy--



		FILO (Stranger) 05-11-00 01:15 No 2615				Re: o-toluidine
						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 (Stranger) 05-12-00 08:35 No 3177				Re: o-toluidine
						If only if superluud were so easy to make :)



		Krypto (Stranger) 05-25-00 02:44 No 8976				Re: o-toluidine
						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 (Stranger) 05-26-00 16:49 No 9659				Re: o-toluidine
						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 (Moderator) 01-07-04 03:03 No 480845				Electrolytic Anthranillic Acid (Rated as: good read)
						The Electrolytic Preparation of Anthranillic Acid Canadian Journal of Research Vol 13, Sec B September 1935, No 3, pp 123-32 Shipley and Calhoun Chemistry is our Covalent Bond

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