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publicationNumber GB-1050737-A
abstract 1,050,737. Indole derivatives. MERCK & CO. Inc. Jan. 29, 1964 [Feb. 1, 1963], No. 2068/66. Divided out of 1,050,728. Heading C2C. Indole-3-acetic acid derivatives of the formula wherein R 1 is an aryl, heterocyclic aryl or substituted aryl or heterocyclic aryl group, e.g. pchlorophenyls, R 2 is a hydrogen atom or a C 1-5 alkyl, C 2-5 alkenyl, aryl, aralkyl, alkaryl or substituted alkyl or aryl radical, R 3 is hydrogen or a C 1-5 alkyl or C 2-5 alkenyl radical and R 5 is a hydrogen or halogen atom or a C 1-5 alkyl, C 1-5 alkoxy, e.g. CH 3 O, haloalkyl, nitro, amino, substituted amino, cyano, aminomethyl, alkylsubstituted amino methyl, mercapto, dialkysulphamoyl or benzyl mercapto radical, are made by reacting the corresponding 1-unsub stituted compound with at least two equivalents of sodium hydride in an inert solvent, cooling the mixture below room temperature, adding the acyl halide of a carboxylic acid of the formula R 1 COOH to form the mixed anhydride of the acid R 2 COOH and the 1-R.CO-indole-3- acetic acid and agitating this in a dilute aqueous hydrogen halide at a temperature below ambient. The exemplified product is 1-p-chlorobenzoyl - 2 - methyl - 5 - methoxyindole - 3 - acetic acid.
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