Sodium Hydroxide → HCID 18447126, compound

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%).

1. additionby adding
2. extractionextracted twice with ethyl acetate/tetrahydrofuran=5/1
3. extractionThe combined extract layer
4. washwas washed with water
5. dry with materiala saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate
6. filtrationfiltered
7. distillationThe solvent was distilled off under reduced pressure
8. concentrationthe resulting concentration residue
9. customwas purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1, 1/1, 1/2)
10. customto obtain a yellow solid
11. customThe solid obtained
12. additionby adding
13. customthe yellow solid precipitated
14. filtrationwas collected by filtration
15. washwashed with diethyl ether
16. customdried under reduced pressure

ORD record

ord-c767eb90d62f4c69a56e0cf6de9d85d3

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2