Synthesis of substituted dinitrophenylketones and phenyl-acetic acids – Part VI

A.B. Sen & P. M. Bhargava

Published in: Journal of the Indian Chemical Society, 1949, 26, 71-72

Abstract:

2:6-Dinitro-4-iodophenyl-acetone and -acetic acid and 2-methyl-3-carbethoxy-5-amino-7-iodoindole have been prepared.

In the previous communications (Sen and Bhargava, this Journal, 1947, 24, 268, 371, 403; 1948, 25, 282, 538) the preparation of a number of halogenated dinitrophenylketones and phenylacetic acids has been described; the method employed was to condense a halogenated dinitrobenzene containing a reactive chlorine atom, with acetoacetic and malonic esters, and to submit the resulting product to hydrolysis. In this paper, this reaction has been extended to the preparation of 2: 6-dinitro-4-iodophenyl- acetone and -acetic acid. The ketone has been characterised by the preparation of its phenylhydrazone; its oxime, however, could not be obtained. The reduction of 2:6- dinitro-4-iodophenylacetoacetic ester by iron powder and water yield an indole derivative.

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Synthesis of substituted dinitrophenylketones and phenyl-acetic acids – Part VI. A B SEN & P M BHARGAVA. Journal of the Indian Chemical Society, 1949, 26, 71-72.

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