Abstract

Harindran Suhanaand S. Rajeswari

DOI : http://dx.doi.org/10.13005/ojc/330668

We have developed a simple route for the synthesis of [4-(3-methyl-1H-indol-2-yl)phenyl](phenyl)methanone from easily available starting materials. The (4-propylphenyl)phenylmethanone was prepared by Friedel Craft’s benzoylation of n-propyl benzene with benzoyl chloride in dichloromethane using aluminium chloride as the Lewis acid catalyst. Side chain bromination with N-bromo succinimide in tetra chloro methane furnished the bromo derivative which on oxidation with bis-tetra butyl ammonium dichromate gave 1, 4–diacyl benzene. The target molecule was obtained through Fischer indole cyclisation of the diacyl benzene namely 1-(4-benzoylphenyl)propan-1-one via the formation of the hydrazone, followed by cyclization in presence of boron trifluoride ethyl etherate in acetic acid. The structure of the target molecule was elucidated by IR, H¹, C¹³ NMR, Mass spectroscopy and elemental analysis. This method proves to be an efficient route for the synthesis of [4-(3-methyl-1H-indol-2-yl)phenyl](phenyl)methanone in high yields, thereby facilitating the generation of potential biologically active compounds.

Fischer indole synthesis; 1, 4-diacylbenzene; Friedel-Craft’s benzoylation; allylic bromination

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