Synthesis of 1-amino-2-methylindoline by Raschig process: Parallel reactions, modeling, and optimization

The reaction between chloramine and 2-methylindoline was studied at pH 12.89, T = 40°C, and for different initial concentrations of reactants. The interaction includes two concurrent bimolecular mechanisms leading to 1-amino-2-methylindoline and 2-methylindole. The rate laws were determined at the first moments of the reaction by using a differential method. By considering the totality of the reactions that occur in the medium, an appropriate mathematical model was developed. It permits to follow the evolution of the system over time and to calculate the final yields of reaction products. An optimization in terms of the initial contents of 2-methylindoline and chloramine was performed. It indicated that the maximum yield of 1-amino-2-methylindoline does not exceed 56%. The results show the limit of the Raschig process for the synthesis of indolic hydrazines in aqueous medium. © 2002 Wiley Periodicals, Inc. Int J Chem Kinet 34: 575–584, 2002