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With iron; ammonium chloride; In ethanol; water; for 1.0h;Reflux;
Second Step [Show Image] To an aqueous 80% ethanol solution (250 mL) of the product (3.00 g, 13.56 mmol) of the first step, ammonium chloride (0.363 g, 6.78 mmol) and iron (7.57 g, 136 mmol) were added, followed by reflux for one hour. After cooling the reaction mixture to room temperature, insoluble substances were filtered through cerite and then washed in turn with ethanol and ethyl acetate. The filtrate was concentrated under reduced pressure and water was added to the resulting residue, and then the precipitated solid was collected by filtration to obtain 2.32 g of methyl 6-amino-1H-indazole-4-carboxylate. 1H-NMR (500 MHz, DMSO-d6) d: 3.89 (s, 3H), 5.52 (s, 2H), 6.77 (dd, 1H, J = 1.8, 1.0 Hz), 7.26 (d, 1H, J = 1.8 Hz), 8.07 (s, 1H), 12.59 (s, 1H).
Third Step [Show Image] To a THF solution (200 mL) of the product (2.28 g, 11.9 mmol) of the second step, a THF solution (1 M, 36 mL) solution of lithium aluminum hydride was added under ice cooling, followed by stirring at room temperature for 20 hours. To the reaction mixture, water (2 mL), an aqueous 15% sodium hydroxide solution (2 mL) and water (5 mL) were sequentially added under ice cooling thereby terminating the reaction. After insoluble substances were filtered through cerite, the filtrate was concentrated under reduced pressure to obtain 1.34 g of (6-amino-1H-indazol-4-yl)methanol. 1H-NMR (500 MHz, DMSO-d6) d: 4.63 (d, 2H, J = 5.6 Hz), 5.0-5.25 (m, 3H), 6.35 (dd, 1H, J = 1.2, 0.4 Hz), 6.46 (dd, 1H, J = 1.6, 0.8 Hz), 7.76 (s, 1H), 12.21 (br, 1H).
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