argox120
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Looking for 2 nitroaniline
Hello, can anybody please point me in the right direction, i need 2 nitro aniline cas 88-74-4 to form an imine derivative of a substance, hope yall
can help me
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chempyre235
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What sources have you searched already? 2-Nitroaniline should be relatively simple to make for the amateur. According to Wikipedia, it can be made
from acetaminophen. Please, use your search engine, and stop asking to be spoonfed. Do your own research first.
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argox120
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clueless person, how can 2 nitroaniline be made from acetaminophen which has a hydroxyl group para to the aniline. since you are so wise here.
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chempyre235
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I apologize. I meant acetanilide, not acetaminophen.
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bnull
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Quote: Originally posted by argox120  | | Hello, can anybody please point me in the right direction, i need 2 nitro aniline cas 88-74-4 to form an imine derivative of a substance, hope yall
can help me |
Do you want to buy or to make it? If the former, you can try @mario840.
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Keras
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One way I see is, starting from aniline, make acetanilide (e.g. with zinc and acetic acid rather than the more expensive and difficult to get acetic
anhydride), then nitrate the acetanilide the standard way, producing a mixture of o- and p-nitroacetanilide. Hydrolyse the 'acetate' moiety by
refluxing in dilute acid to get a mixture of o- and p- nitroaniline, which can be separated on a chromatographic column filled with alumina using
toluene as eluent (easy, two yellow rings, o- comes first).
Because of steric hinderance, the yield of o-nitroaniline is not that great, much less than p-nitroaniline, but eh. Maybe you could sulphonate the
acetanilide, which would block the para position before nitrating. Then on hydrolysis both the sulphonate and the acetate group would be released,
giving pure o-nitroaniline. No promise, though.
Aniline needs be protected from protonation by the acid nitrating mixture, otherwise you end up with m-nitroaniline.
[EDIT: Apparently, there’s an easy separation process whereby the mixture o-/p- is dissolved in methanol. On cooling, p- will crystallise, while o-
stays in solution and can be isolated later.]
[Edited on 26-3-2025 by Keras]
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chempyre235
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Orgsyn has a synthesis using the sulfonated derivative followed by hydrolysis.
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