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Q: Isomer development during reduction ( No Answer,   4 Comments )
Question  
Subject: Isomer development during reduction
Category: Science > Chemistry
Asked by: sandy7021-ga
List Price: $2.00
Posted: 14 Jun 2004 01:40 PDT
Expires: 14 Jul 2004 01:40 PDT
Question ID: 360719
Is it possible that isomer Meta Chloro Aniline devoleps during
reduction of 2,5-DCNB for manufacturing 2,5-DCA
Answer  
There is no answer at this time.

Comments  
Subject: Re: Isomer development during reduction
From: dr_bob-ga on 14 Jun 2004 13:37 PDT
 
If you want a precise answer you'll need to explain a little first.

1.) What reagents are you using?
2.) by isomer meta chloro anilline, you mean 3 chloroaniline.  as in 1
chlorine, the other two removed?

Just as you've described, IMO, it would be pretty hard to happen under
normal conditions.
Subject: Re: Isomer development during reduction
From: sandy7021-ga on 15 Jun 2004 23:20 PDT
 
We are adding Thiourea as a catalyst and yes it is 3-Chloro Aniline
which is being developed during reduction.
Subject: Re: Isomer development during reduction
From: dr_bob-ga on 16 Jun 2004 11:11 PDT
 
ok...now you've piqued my curiosity.

i haven't got a clue, but here's where I would start.

first, get said spectra on putative 3-chloro aniline:  proton, c13,
ms(cl's will be a dead giveaway).

a.) make sure indeed that starting materials are what you think they
are and apply all common sense.

b.) the ortho chloro's on 2,5 dcnb are quite reactive to SNar
substitution. (As in alcohol + cook=ether)

c.) I would think more likely you get thiourea addition-elimination to
one of the chloros then reaction with the reduced nitro. (think
nitroso, amine, etc, think amino benzathiazole)

Now you just gotta blow off half of that heterocycle to get 3 chloroanilline.

chugs,
Subject: Re: Isomer development during reduction
From: acrh2-ga on 17 Jun 2004 23:38 PDT
 
I'm sure 15-N tests would prove you right :)

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