反应详情

温度

85 °C

To a mixture of 2-[(5-methyl-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]acetonitrile (0.66 g, 1.86 mmol) in dry THF (120 mL) is added borane-methylsulfide complex (0.53 mL, 5.6 mmol). The mixture is refluxed at 85° C. for 18 h. The mixture is removed from heat and methanol is slowly added until gas evolution ceased. The solvents are removed under vacuum and methanol (5 mL) is added and again removed. The residue is dissolved in CH2Cl2/CH3OH (1:2 15 mL). Conc. HCl (2 mL) is added and the mixture heated at 65° C. for 1 h. The mixture is removed from heat and neutralized with aqueous potassium carbonate then partitioned between water and CH2Cl2. The organic layer is washed with water, dried over magnesium sulfate, and concentrated. Column chromatography (70 g silica gel) using CH3OH/CH2Cl2 (4:96) as eluent gave 0.444 g (67%) of the title compound;

1. additionis added borane-methylsulfide complex (0.53 mL, 5.6 mmol)
2. customThe mixture is removed
3. temperaturefrom heat
4. additionmethanol is slowly added until gas evolution
5. customThe solvents are removed under vacuum and methanol (5 mL)
6. additionis added
7. customagain removed
8. dissolutionThe residue is dissolved in CH2Cl2/CH3OH (1:2 15 mL)
9. additionConc. HCl (2 mL) is added
10. temperaturethe mixture heated at 65° C. for 1 h
11. customThe mixture is removed
12. temperaturefrom heat
13. customthen partitioned between water and CH2Cl2
14. washThe organic layer is washed with water
15. dry with materialdried over magnesium sulfate
16. concentrationconcentrated