Thionyl Chloride → 4-Methoxy-2-nitrobenzoyl chloride

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A mixture of 4-methoxy-2-nitrobenzoic acid 1 (1.0 g) and thionyl chloride (5 mL) was heated at 75° C. for overnight under nitrogen atmosphere. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was evaporated at 40° C. under vacuum to give 4-methoxy-2-nitrobenzoyl chloride as a yellow solid which was used in the next step without further purification. To a solution of 4-methoxy-2-nitrobenzoyl chloride (1.0 g) in 10 mL THF was added ammonium hydroxide (5 mL) drop-wise (exothermic). The resulting mixture was stirred at room temperature for 30 min. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was evaporated to give 4-methoxy-2-nitrobenzamide 2 which was purified by triturating with methyl tert-butyl ether. Pink solid (1.05 g, 100%). 1H NMR (400 MHz, CDCl3): δ 3.89 (s, 3H); 5.87 (br s, 2H); 7.13-7.15 (m, 1H); 7.25-7.26 (m, 1H); 7.47-7.52 (m, 1H).

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