Synthesis of indigo from anthranilic acid - reaction not taking place I was trying to synthesise indigo via the Heumann indigo synthesis (II.), which involves heating antrhanilic acid and chloroacetic acid, both dissolved in isopropanol. After heating up, a hydroxide or another strong base is added to form indigo

I have slightly altered the synthesis process, added trichloroacetic acid instead of chloroacetic, and also added more reactants to tilt the equilibrium towards the product.

The problem is, that any signs of reaction have taken place after more than 3 hours

I have discussed the issue with my chemistry teacher, and he said that the trichloroacetic acid had been of poor quality (made 1990, majority of the original crystals dissolved, turned to brownish liquid). I also think could be simply stopped by the forming of salt (sodium trichloroacetate) and that being unable to interact with anthranilic acid.

I'm very desperate about this. Do you have any thoughts on how to get that reaction going?
Trichloroacetic acid was definitely the wrong way to go.

The reason is the chloroacetic acid is alkylating your anthranilic acid, adding the missing carbons Ben Norris comments on.  Ttrichloroacetic acid is not a great alyklating agent, owing to steric bulk.

If you are dead set against working it up and separating your anthranilic acid, you might try just adding the chloroacetic acid.  

Otherwise clean it up and start over.