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With ammonium formate; iron; In ethanol; water; at 90℃; for 2h;
To a solution of <strong>[6494-19-5]3-methyl-6-nitroindazole</strong> (0.4 g, 2.24 mmol) in ethanol (EtOH) (10 mL) and H2O (5 mL) was added Iron (0.63 g, 11.22 mmol) and ammonium formate (1.4 g, 22.4 mmol). After heating at 90° C. for 2 h, the mixture was diluted with EtOAc, excess iron was removed by filtration, and the filtrate was washed sequentially with water, sat. NaHCO3, and brine, before it was dried and concentrated to give 6-amino-3-methylindazole (0.27 g).
With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; for 10h;
Second Step [Show Image] To an ethyl acetate solution (50 mL) of the product (1.17 g, 6.60 mmol) of the first step, 10percent Pd-C (0.46 g) was added, followed by stirring under a hydrogen gas flow at room temperature for 10 hours. The insoluble substances were filtered through cerite and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:n-hexane = 3:1) to obtain 0.57 g of 6-amino-3-methylindazole. 1H-NMR (CDCl3) d: 2.50 (s, 3H), 6.4-6.65 (m, 2H), 7.43 (d, 1H, J = 8.4 Hz), 9.35 (br, 1H).
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