Condensation of 2-methylindole with acetophenones: An unexpected formation of 2-arylanilines

Abstract

2-Methylindole condenses with acetophenones under acidic conditions to produce 2-arylanilines in moderate to good yields. The reaction proceeds well with a range of 3′- and 4′- substituted acetophenones (fluoro-, chloro-, bromo-, iodo-, methyl, methoxy), and select 2′- substituted ones (fluoro-, methoxy-). No products were obtained with nitro- substitution in any position.

GRAPHICAL ABSTRACT

Keywords:

• 2-methylindole
• acetophenones
• acid-catalyzed condensation
• anilines

Additional information

Funding

The authors thank the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for generous financial support of this project.