Methanol → 2-(Methylthio)-5-nitropyridine

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Reaction Steps

The methanol solution of methyl sodium sulfide (6 g, 86 mmol) was added portionwise at 0° C. into the methanol solution of 2-chloro-5-nitropyridine (2 g, 13 mmol). Then, the reaction mixture was heated to room temperature and stirred for 14 hours. The reaction mixture was poured into 20 mL water, and extracted with ethyl acetate 20 mL for three times. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated. The residual was recrystallized in diethyl ether to yield yellow solid 2-(methylthio)-5-nitropyridine (2 g, 12 mmol). 1H-NMR (300 MHz, CDCl3): δ 2.64 (3H, s), 7.28-7.32 (1H, m), 9.24 (1H, dd), 9.26 (1H, d); LC-MS m/z: 171 [M++1]; purity (HPLC)>95%.

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