Hello,
I want to synthesize (3-indolyl)acetic acid from gramine, i.e. a tertiary amine group to a carboxylic acid group in 3 steps. I was thinking of starting with the conversion of the tertiary amine group to a quaternary ammonium cation and then go on to the elimination of the salt to to an alkene via a Hofmann elimination. With heat, KMnO4, OH- and acid it should be possible to break the alkene into a carboxylic acid + formaldehyde. What I did not take into consideration is that the nitrogen in (3-indolyl)acetic acid is bonded to a CH2 that's bonded directly to an aromatic 5-membered ring, hence making it impossible to carry out the Hofmann elimination. Now, without success, I have discovered nothing in textbook and online papers that illuminates this reactivity.