反应详情

温度

80 °C

5′-Isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-carbaldehyde (8.0 g), hydroxylamine hydrochloride (3.45 g) and pyridine (28 ml) are dissolved in ethanol (140 ml), and the mixture is stirred at 80° C. for 1 hour. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and a 1N-hydrochloric acid, and the mixture is separated, and the organic layer is washed with a saturated sodium carbonate, water and a saturated brine, and the mixture is dried over magnesium sulfate and concentrated under reduced pressure. Thereto are added ethyl acetate and a 1N-hydrochloric acid, and the mixture is separated, and the organic layer is washed with a 1N-hydrochloric acid, a saturated sodium carbonate, water and a saturated brine, and the mixture is dried over magnesium sulfate and concentrated under reduced pressure. The residue is dissolved in methanol (100 ml), and thereto is added Raney nickel, and the mixture is stirred under hydrogen atmosphere at room temperature for 30 minutes and at 50° C. overnight. The reaction solution is cooled to room temperature, and Raney nickel is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (chloroform:methanol=1:0→23:2) to give C-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-yl)-methylamine (5.50 g). MS (m/z): 324 [M+H]+

1. temperatureThe reaction solution is cooled to room temperature
2. customa 1N-hydrochloric acid, and the mixture is separated
3. washthe organic layer is washed with a saturated sodium carbonate, water
4. dry with materiala saturated brine, and the mixture is dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. additionThereto are added ethyl acetate
7. customa 1N-hydrochloric acid, and the mixture is separated
8. washthe organic layer is washed with a 1N-hydrochloric acid
9. dry with materiala saturated sodium carbonate, water and a saturated brine, and the mixture is dried over magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. dissolutionThe residue is dissolved in methanol (100 ml)
12. additionis added Raney nickel
13. stirringthe mixture is stirred under hydrogen atmosphere at room temperature for 30 minutes and at 50° C. overnight
14. temperatureThe reaction solution is cooled to room temperature
15. customRaney nickel is removed by filtration
16. concentrationthe filtrate is concentrated under reduced pressure
17. customThe residue is purified by silica gel column chromatography (chloroform:methanol=1:0→23:2)