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With sulfuric acid; nitric acid In water at 0 - 50℃; for 3.25 h;
To a solution of 2-amino-3-(trifluoromethyl)pyridine (2 g, 12.34 mmol) in cone <n="242"/>sulfuric acid (10 mL) at 0 0C was added dropwise fuming nitric acid (0.56 mL, 12.34 mmol). After 15 min, the reaction was allowed to stir at room temperature. After 1 hour, the mixture was heated to 50 0C. After 2 hours, the reaction was cooled to room temperature and slowly poured into ice-water (200 mL). The precipitate was filtered and dried under high vacuum to give 5-nitro-3-trifluoromethyl-pyridin-2-ylamine (1.92 g, 75percent). 1H NMR (d6-DMSO, 300 MHz) δ 8.02 (brs, 2H), 8.38 (d, IH, J = 2.6 Hz), 9.04 (d, IH, J = 2.6 Hz); MS (ESI) m/z = 208 (MH+).
A solution of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (15 g, 66.2 mmol) and ammonia solution in MeOH (7 N, 150 mL, 1.05 mol) was stirred at room temperature for 14 h. After completion of the reaction, reaction mixture was concentrated under vacuum and residue was diluted with water (100 mL) and aqueous phase was extracted with ethyl acetate (100 mL x 3), combined organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was rotary evaporated to afford 11 g (80percent) of the titled product as yellow solid.1HNMR (400 MHz, DMSO- d6) U9.06 (d, J = 2.7 Hz, 1H), 8.40 (d, J = 2.7 Hz, 1H), 8.04 (s, 2H); ESI-MS (m/z) 208.33 (MH)+.
With sulfuric acid; nitric acid; In water; at 0 - 50℃; for 3.25h;
To a solution of 2-amino-3-(trifluoromethyl)pyridine (2 g, 12.34 mmol) in cone <n="242"/>sulfuric acid (10 mL) at 0 0C was added dropwise fuming nitric acid (0.56 mL, 12.34 mmol). After 15 min, the reaction was allowed to stir at room temperature. After 1 hour, the mixture was heated to 50 0C. After 2 hours, the reaction was cooled to room temperature and slowly poured into ice-water (200 mL). The precipitate was filtered and dried under high vacuum to give 5-nitro-3-trifluoromethyl-pyridin-2-ylamine (1.92 g, 75%). 1H NMR (d6-DMSO, 300 MHz) delta 8.02 (brs, 2H), 8.38 (d, IH, J = 2.6 Hz), 9.04 (d, IH, J = 2.6 Hz); MS (ESI) m/z = 208 (MH+).
N-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
46%
With dmap; triethylamine; In dichloromethane; at 20℃; for 1.0h;
To a stirred solution of <strong>[1121056-94-7]5-nitro-3-(trifluoromethyl)pyridin-2-amine</strong> (2 g, 9.66 mmol) in dichloromethane (20 mL) was added DMAP (1.29 g, 10.62 mmol), Et3N (2.69 mL, 19.31 mmol) and acetyl chloride (0.758 mL, 10.62 mmol) at room temperature and the resulting reaction mixture was stirred for 1H. After completion of the reaction, reaction mixture was neutralized with aqueous (1 M) solution of potassium carbonate. Aqueous phase was extracted with ethyl acetate (20 mL x 3), combined organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was rotary evaporated and residue was purified by flash column chromatography (silica gel) to afford 1.1 g (46%) of the titled product as yellow solid. 1HNMR (400 MHz, DMSO-d6) U10.73 (s, 1H), 9.47 (d, J = 2.6 Hz, 1H), 8.84 (d, J = 2.6 Hz, 1H), 2.14 (s, 3H); ESI-MS (m/z) 249.80 (MH)
A solution of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (15 g, 66.2 mmol) and ammonia solution in MeOH (7 N, 150 mL, 1.05 mol) was stirred at room temperature for 14 h. After completion of the reaction, reaction mixture was concentrated under vacuum and residue was diluted with water (100 mL) and aqueous phase was extracted with ethyl acetate (100 mL x 3), combined organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was rotary evaporated to afford 11 g (80percent) of the titled product as yellow solid.1HNMR (400 MHz, DMSO- d6) U9.06 (d, J = 2.7 Hz, 1H), 8.40 (d, J = 2.7 Hz, 1H), 8.04 (s, 2H); ESI-MS (m/z) 208.33 (MH)+.
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