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Author: Subject: Friedal craft reaction with anilides.
Sunil Sharma
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[*] posted on 21-1-2013 at 06:45
Friedal craft reaction with anilides.


I have questions regarding this reaction (see Attachment).
1. Is this reaction possible.
2. If yes can anybody suggest me what should be the reaction conditions.

Because i am trying this reaction from many days but i am not sucessfull.
One information i want to share that this reaction with chlorobenzene going very easily.

Untitled.jpg - 17kB

[Edited on 21-1-2013 by Sunil Sharma]
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Adas
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[*] posted on 21-1-2013 at 07:17


I think that the nitrogen is being acetylated instead of the benzene ring or the AlCl3 decomposes the whole substance somehow.

[Edited on 21-1-2013 by Adas]




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Nicodem
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21-1-2013 at 07:55
Sunil Sharma
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[*] posted on 21-1-2013 at 08:16


Thanx for reply....
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kavu
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[*] posted on 21-1-2013 at 08:32


You can do such reactions, amide nitrogen is not nearly as nucleophilic compared to an amine. These reactions have been carried out and there are some refereces. Acylation of acetanilide has been discussed in the following article 10.1016/j.tet.2011.05.118

The N-acylation has also been discussed and seems to require a high temperature at around 220­ °C (Birtwell
Journal of the Chemical Society, 1949, p. 2561).

[Edited on 21-1-2013 by kavu]
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