[Plumbum]

Hi there

I synthesized anthranillic acid and I wondered what side products might there be. I used Phtalamide and bromine.

Thank u

[TheUnassuming]

Can you give more details at to the specific reaction conditions?

[Plumbum]

Sure.

Here you go

[Plumbum]

any ideas?

[TheUnassuming]

I'd imagine most of your side reactions will arise from the hofmann rearrangement with an ortho-carboxylate right there ready to react.

[Plumbum]

I don't really understand , what side product might there be ?

[sjb]

I don't really understand , what side product might there be ?

Consider the mechanism. Are there any intermediates that may for instance be captured by alternative reagents (http://en.wikipedia.org/w/index.php?title=Hofmann_rearrangement&oldid=663432617 )

(edit link, sjb)

[Plumbum]

I dont know thats why im asking xD

[orgopete]

I would say it depends. I think regular Hoffmann reactions may have a urea as a by-product. That may not be as likely due to the intramolecular reaction that probably occurs. However, just as reaction of the intermediate that leads to urea can occur, a similar reaction of anthranilic acid with an intermediate can give a different product.

I can also guess that if the amount of bromine were in excess, anthranilic acid could react further with it.