反应详情

温度

80 °C

N-(2-methyl-5-nitrophenyl)-4-(pyridine-3-yl)pyridine-2-amine (3.07 g, 10.0 mmol), hydrazine monohydrate (1.54 g of 65% solution in water, 20.0 mmol), FeCl3 (21 mg, 0.13 mmol), and activated carbon (0.2 g) were dissolved in a mixture of methanol (200 mL) and ethyl acetate (100 mL). The reaction mixture was heated to 80° C. with stirring and maintained for 24 hours. The reaction mixture was cooled own to room temperature. The insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (150 mL) and washed with water (150×2). The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the resulting residue was purified by column chromatography (biotage: DMC/Methanol, 1-8%, 25 CV). The product was obtained (1.57 g, yield: 56.4%) as a yellow solid and 0.53 g starting material of N-(2-methyl-5-nitrophenyl)-4-(pyridine-3-yl)pyridine-2-amine was recovered; 1H NMR (500 MHz, CDCl3) δ 2.28 (s, 3H), 3.68 (s, 2H), 6.45 (d, 1H), 6.95 (s, 1H), 7.02 (d, 1H), 7.18 (d, 1H), 7.45 (m, 1H), 7.35 (d, 1H), 7.65 (s, 1H), 8.37 (d, 1H), 8.52 (d, 1H), 8.74 (d, 1H), 9.28 (s, 1H). LC-MS (m/z) calculated, 277.3. found, 278.2 [M+H]+.

1. temperaturemaintained for 24 hours
2. temperatureThe reaction mixture was cooled own to room temperature
3. customThe insoluble materials were removed by filtration
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe resulting residue was dissolved in ethyl acetate (150 mL)
6. washwashed with water (150×2)
7. dry with materialThe organic phase was dried over anhydrous Na2SO4
8. customThe solvent was removed under reduced pressure
9. customthe resulting residue was purified by column chromatography (biotage: DMC/Methanol, 1-8%, 25 CV)
10. customThe product was obtained (1.57 g, yield: 56.4%) as a yellow solid and 0.53 g
11. customwas recovered