* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With palladium 10% on activated carbon; hydrogen In ethanol
To an EtOH solution (400 mL) containing 10percent Pd/C (7.46 g, 70.1 mmol) in a Parr vessel was added 1 -fluoro-3-methoxy-2-nitrobenzene (40.0 g, 234 mmol). The vessel was evacuated under vacuum and refilled with hydrogen (50 psi). The reaction was shaken 5 h, filtered through Celite? and concentrated to give the title compound (30.0 g, 83percent) as a colorless oil. 1H NMR (400 MHz, CDCI3) δ 3.75 (br s, 2 H), 3.86 (s, 3 H), 6.58-6.71 (m, 3 H); LC-MS (LC-ES) M+H = 142.
Reference：
[1] Patent: WO2018/69863, 2018, A1, . Location in patent: Page/Page column 248
[2] Journal of the American Chemical Society, 1932, vol. 54, p. 2973,2976
[3] Journal of the Chemical Society, 1931, p. 981
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1641 - 1653
2
[ 4920-80-3 ]
[ 446-61-7 ]
Reference：
[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1641 - 1653
3
[ 16554-47-5 ]
[ 446-61-7 ]
Reference：
[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1641 - 1653
4
[ 15865-57-3 ]
[ 446-61-7 ]
Reference：
[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 11, p. 1641 - 1653
5
[ 385-01-3 ]
[ 446-61-7 ]
Reference：
[1] Journal of the American Chemical Society, 1932, vol. 54, p. 2973,2976
With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20℃;
Reference Example 98 3-Amino-4-chloro-N-(2-fluoro-6-methoxyphenyl)-N-methylbenzenesulfonamide To a mixture of 2-fluoro-6-methoxyaniline (0.56 g), sodium hydrogen carbonate (0.67 g) and water (2 mL) in tetrahydrofuran (20 mL) was added a solution of 4-chloro-3-nitrobenzenesulfonyl chloride (1.0 g) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane - n-hexane/ethyl acetate = 2/3) to give 4-chloro-N-(2-fluoro-6-methoxyphenyl)-3-nitrobenzenesulfonamide (0.56 g). This material was dissolved in N,N-dimethylformamide (15 mL). To the solution were added methyl iodide (0.15 mL) and sodium hydride (55%, 75 mg) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane - n-hexane/ethyl acetate = 1/1) to give 4-chloro-N-(2-fluoro-6-methoxyphenyl)-N-methyl-3-nitrobenzenesulfonamide (0.4 g). This material was dissolved in tetrahydrofuran (3 mL). To the solution were added methanol (3 mL) and nickel(II) bromide (12 mg). To the mixture was added sodium borohydride (0.12 g) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes, and then stirred at room temperature for 1 hour. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane - n-hexane/ethyl acetate = 1/4) to give the title compound (0.3 g).
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