Sodium Hydroxide → HCID 18447126, compound

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Reaction Steps

Under nitrogen, the 5-(2-chloro-4-nitrophenoxy)-4-methyl-1H-indazole (120 mg, 0.395 mmol) obtained in Example 738 was dissolved in ethanol (6 ml), followed by adding thereto tin(II) chloride dihydrate (446 mg, 1.98 mmol), and the resulting mixture was stirred at 80° C. for 1 hour. The reaction solution was cooled to room temperature and then poured into water, and the resulting mixture was adjusted to pH>8 with a 1N aqueous sodium hydroxide solution and extracted twice with ethyl acetate/tetrahydrofuran=5/1. The combined extract layer was washed with water and then a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1, 1/1, 1/2) to obtain a yellow solid. The solid obtained was dissolved in 1,4-dioxane (2 ml), followed by adding thereto a 4N-hydrochloric acid/1,4-dioxane solution (2 ml), and the resulting mixture was stirred at room temperature. Thereafter, diethyl ether (about 15 ml) was added thereto and stirred, and the yellow solid precipitated was collected by filtration, washed with diethyl ether and then dried under reduced pressure to obtain 3-chloro-4-[(4-methyl-1H-indazol-5-yl)oxy]aniline monohydrochloride (45 mg, yield 42%).

Provenance & Evidence