4- Nitro-3-methylbenzoic acid

According to Kholevo and Eitington [130] the nitratiton of m- xylene leads to formation of 4-nitro-3-methylbenzoic acid. Here the mercuric nitrate also enhances the oxidation of the methyl group. 

An excellent method for producing methyl indole-4-carboxylate from commercially available 3-nitro-2-methylbenzoic acid involves reduction of an intermediate nitroenamine (57). 

Bromo methylbenzoic acid isobutyl ester fenpyroximate p Bromo nitro benzene chlorbromuron 4 Bromophenol silafluofen a Bromo a phenyl acetone diphacinone Bromo pinacolone diclobutrazol, triadimefon Bromo propane penconazole... 

Although 2-bromo-4-nitrotoluene has been obtained by several routes, it is most easily prepared by bromination of />-nitro-toluene.2 The procedure given is adapted from that described by Cavil .3 2-Bromo-3-methylbenzoic acid has not been prepared by any other means evidence for its structure is presented elsewhere.4... 

To a hot solution of 12.1 g. (0.05 mole) of 3 nitro-4-methylbenzo-phenone (p. 228) in 300 ml. of ethanol is added dropwise a hot solution of 22.5 g. of crystalline sodium sulfide in 30 ml. of ethanol and 30 ml. of water. The reaction mixture is poured into 500 ml. of water, and the precipitated oil solidifies on cooling. The solid product is suspended in 600 ml. of boiling water and treated with concentrated hydrochloric acid until no more solid dissolves. The mixture is filtered rapidly, and the filtrate is treated with excess aqueous ammonia. The precipitated solid is recrystallized from methanol to give 9 g. (85%) of amine, m.p. 109-110°. 

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