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5-Chloro-3-nitro-2-pyridinamine (5.0 g, 28.8 mmol) was dissolved in cone. HCI (50 mL) and cooled to -10 0C in an ice-salt bath. Sodium nitrite (4.97 g, 72 mmol) in water (10 mL) was added dropwise to the cooled solution over 1 h and stirred at 0 C for 1 h longer. The reaction mixture was cooled to -10 0C in an ice-salt bath and neutralized with 2N sodium hydroxide to pH 9.0 keeping the temperature below 0 0C. EtOAc (150 mL) was added and the mixture was filtered. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to afford the title compound as 3.36 g (60% yield) of a light brown solid; 1H NMR (cfe-DMSO) δ 8.62 (d, 1 H, 2.5 Hz), 8.26 (d, 1 H, 2.2 Hz).
58.5%
With hydrogenchloride; sodium nitrite; In water; at -10 - 0℃; for 1.5h;
<strong>[5409-39-2]5-chloro-3-nitropyridine-2-amine</strong> 10.0g of (57.6 mmol) was dissolved in concentrated hydrochloric acid 100 mL, and stirred at -10 C.. Here, sodium nitrite 9.94g of (144 mmol) Yuki dropwise over 30 minutes a liquid obtained by dissolving water 20 mL, after the addition, the mixture was stirred 1 hour at 0 C.. By adding 1N aqueous sodium hydroxide solution to the reaction solution and pH 9, and extracted with ethyl acetate. Insolubles were removed by filtration, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. Filtered and the filtrate was evaporated under reduced pressure to give the title compound 6.50g of (58.5% yield) as a solid.
58.5%
<strong>[5409-39-2]5-chloro-3-nitropyridine-2-amine</strong> 10.0g of (57.6 mmol) was dissolved in concentrated hydrochloric acid 100 mL, and stirred at -10 C.. Here, sodium nitrite 9.94g of (144 mmol) add dropwise over 30 minutes a liquid obtained by dissolving water 20 mL, after the addition, the mixture was stirred 1 hour at 0 C.. By adding 1N aqueous sodium hydroxide solution to the reaction solution and pH 9, and extracted with ethyl acetate. Insolubles were removed by filtration, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. Filtered and the filtrate was evaporated under reduced pressure to give the title compound 6.50g of (58.5% yield) as a solid.
58.5%
With hydrogenchloride; sodium nitrite; In water; at -10 - 0℃; for 1.5h;
(Step 1) 2,5-Dichloro-3-nitropyridine 5-Chloro-3-nitropyridin-2-amine (10.0 g, 57.6 mmol) was dissolved in concentrated hydrochloric acid (100 mL), and the solution was stirred at -10C. A solution of sodium nitrite (9.94 g, 144 mmol) dissolved in water (20 mL) was added dropwise thereto over 30 minutes. After the completion of the addition, the mixture was stirred at 0C for 1 hour. The pH of the reaction solution was adjusted to 9 by the addition of a 1 N aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. Insoluble matter was removed by filtration, and the organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After filtration, the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (6.50 g, yield: 58.5%) as a solid. 1H-NMR (CDCl3) δ: 8.60 (1H, d, J = 2.9 Hz), 8.24 (1H, d, J = 2.6 Hz).
With tert.-butylnitrite; copper dichloride; In acetonitrile; at 70℃; for 17.5h;
Example 14; Preparation of Compound 14A ; To a stirred solution of tert-butyl nitrite (55.2 ml, 466 mmol) and anhydrous Cu(II)Cl2 (50.0 g, 372 mmol) in CH3CN (500 mL), maintained at 70 C., was added 2-amino-5-chloro-3-nitrobenzene 38 (53.6 g, 310 mmol) portionwise over 30 min. The mixture turned from greenish to brown, and gas evolution was observed. Stirring at 70 C. was continued for 16 h. The reaction mixture was cooled and partitioned between 20% aqueous HCl (400 mL) and diethyl ether (1 l). Layers were separated, and the aqueous phase was extracted with EtOAc (500 mL). Combined extracts were washed successively with 20% aqueous HCl (200 mL) and brine (300 mL), dried over anhydrous MgSO4, filtered and concentrated under vacuum. The residue was flash chromatographed on silica gel, eluting with EtOAc-hexanes (1:4), to provide 17.3 g of compound 39 as a yellow oil, which spontaneously crystallized upon standing at room temperature.
With potassium carbonate; In acetonitrile; at 80℃; for 2h;
2,5-Dichloro-3-nitropyridine (WXOO1 -1) (464.42 mg, 1.04 mmol) and compound WXOO1-2 (569.40 mg, 2.08 mmol) were dissolved in acetonitrile (3.00 mE) at room temperature, followed by the addition of potassium carbonate (287.48 mg, 2.08 mmol). The reaction mixture was heated to 80 C. and stirred for 2 hours. Afier the reaction, the mixture was cooled to room temperature, diluted with water (10 mE) and extracted with ethyl acetate (5 mEx2). The organic phases were combined and dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent. The obtained residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate=1 0/1-2/1, volume ratio) to obtain the target product WXOO1 -3. MS-ESI mlz:430.0 [M+H].
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