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Topic: How to synthesise aniline with a SO3H group ortho to NH2?  (Read 2291 times)

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Offline Oliver

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How to synthesise aniline with a SO3H group ortho to NH2?
« on: June 14, 2013, 04:46:35 AM »
Starting from benzene. I've been dwelling over this for a few days.

I tried sulfonating aniline but I think that gives the ortho product in a low yield. I also considered protecting aniline with acetic anhydride then sulfonating then removing the protection with acid then sulfonating again to get a o,p-disubstituted aniline then desulfonating but that would remove both the -SO3H groups, not just the para group.

Offline Hunter2

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Offline Oliver

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Re: How to synthesise aniline with a SO3H group ortho to NH2?
« Reply #2 on: June 14, 2013, 09:02:35 AM »
Interesting. Thank you.

Offline opsomath

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Re: How to synthesise aniline with a SO3H group ortho to NH2?
« Reply #3 on: June 14, 2013, 09:59:26 AM »
If there is an Org Syn paper for making your stuff, use it. It's the best source for synthetic procedures I've ever seen.

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