In a 500 mL round-bottom flask equipped with a mechanical stirrer and thermometer, 10.0 g (0.0386 mol) of 5-methyl-2-((2-nitrobenzene)amino)thiophene-3-carboxynitrile (1) and 100 mL of ethanol were added. Then 7.4 g (0.062 mol) of tin powder and 84 mL of 4M hydrochloric acid were added, and the mixture was stirred at 50 °C for 0.5 h. The temperature of the reaction mixture was raised to 85 °C, and stirring was continued for 4 h. The mixture was then cooled to 25 °C and stirred for another 8 h, which resulted in the precipitation of a solid. The precipitated crystals were collected, washed with 20 mL of ethanol, and dried under vacuum. 9.8 g (96%) of 2-methyl-2-(nitrobenzene) ...
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