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?