Hydrazine → 6-Methoxy-1H-indazole

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A mixture of 2-fluoro-4-methoxybenzaldehyde (1 g, 6.5 mmol) and hydrazine (7 mL) was heated to reflux for 4 h. The mixture was extracted with CH2Cl2. The combined organic layers were washed with water, brine, concentrated in vacuo, and purified by column chromatography (elution with PE/EtOAc=5:1) to afford 6-methoxy-1H-indazole (intermediate 42) (568 mg, 59%) as a yellow solid. HPLC: 99%, RT 2.159 min. MS (ESI) m/z 149.1[M+H]+.

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