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Organic chemistry- adding amine group to benzene

  1. Sep 6, 2016 #1
    Is it possible to do a Friedel-Crafts reaction on a benzene and get a substituent on the benzene ring from that, and then afterwards add an NH2 group ortho? I know you cant add NH2 first and then do Friedel-Crafts because anilines cannot undergo Friedel-Crafts. Please advice. Thanks in advance.
     
  2. jcsd
  3. Sep 7, 2016 #2

    DrDu

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    FC-alkylation or acylation?
     
  4. Sep 7, 2016 #3
    For an acylation.
    I'm just trying to find a way to get the NH2 group on the ring, but I can't figure out how.
     
  5. Sep 8, 2016 #4

    DrDu

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    Try to protect the amine converting it to an amide before FC reaction.
    You could also try some other route like enole condensation to some anthranilic acid ester. Btw, the amino group in anthranilic acid is introduced via a Hofmann rearangement starting from phthalic acid amide.
     
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