Organic chemistry- adding amine group to benzene

In summary, the conversation discusses the possibility of performing a Friedel-Crafts reaction on a benzene ring to add a substituent, followed by adding an NH2 group in the ortho position. It is mentioned that this cannot be achieved by adding the NH2 group first, as anilines cannot undergo Friedel-Crafts. The suggestion is made to protect the amine before the reaction, or to try another method such as enole condensation or a Hofmann rearrangement.
  • #1
AnaK123
2
0
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 can't add NH2 first and then do Friedel-Crafts because anilines cannot undergo Friedel-Crafts. Please advice. Thanks in advance.
 
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  • #2
FC-alkylation or acylation?
 
  • #3
DrDu said:
FC-alkylation or acylation?
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.
 
  • #4
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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Related to Organic chemistry- adding amine group to benzene

1. What is the purpose of adding an amine group to benzene in organic chemistry?

The addition of an amine group to benzene allows for the creation of aromatic amines, which are important building blocks in the synthesis of various organic compounds. It also increases the reactivity of the benzene ring, allowing for further chemical modifications.

2. How is the amine group added to benzene in organic chemistry?

The amine group is typically added to benzene through a substitution reaction, where a hydrogen atom on the benzene ring is replaced by the amine group. This can be achieved through the use of various reagents and catalysts, such as nitrous acid or Friedel-Crafts catalysts.

3. What are the properties of aromatic amines produced by adding an amine group to benzene?

Aromatic amines are typically colorless liquids or solids with a distinct, often pungent odor. They have a higher boiling point and are more soluble in water compared to their non-aromatic counterparts. They also exhibit higher stability and reactivity due to the resonance effect of the benzene ring.

4. What are the applications of aromatic amines produced by adding an amine group to benzene?

Aromatic amines have a wide range of applications in various industries, including pharmaceuticals, dyes and pigments, and agrochemicals. They are also used as intermediates in the synthesis of other organic compounds, such as polymers and plastics.

5. Are there any safety concerns when working with aromatic amines produced by adding an amine group to benzene?

Yes, aromatic amines can be toxic and carcinogenic, especially when inhaled or absorbed through the skin. It is important to handle them with caution and follow proper safety protocols, such as wearing protective gear and working in a well-ventilated area.

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