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When 3-nitro-o-xylene was oxidised with chromyl acetate, the methyl group remote from the nitro-group was attacked, yielding 2-methyl-3-nitrobenzylidene diacetate. The adjacent methyl group reacted with diethyl oxalate under the conditions of the Claisen condensation; oxidation of the product gave 2-methyl-6-nitrophenyl-acetic acid which, on reductive cyclisation, gave 4-methyloxindole.
V. Askam and R. H. L. Deeks, J. Chem. Soc. C, 1969, 1935 DOI: 10.1039/J39690001935
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