The chlorination of 5-substituted indoles (OCH3, CH3, Br, CN, N02) with NaOCl was studied. Mixtures of N-chloro- and N-chloro-3-chloro-indoles were formed, Indoles reacted with OCl- in a SEi process to give N-chloroindoles. This reaction was favored by substituents which increased the acidity of the indolic N-H. Indoles or their conjugate bases also reacted with HOCl in a SE2 reaction to give 3-chloroindoles which were then converted to their N-chloro derivatives with excess NaOCl.
All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Organic Chemistry