反应详情

温度

60 °C

To a 3-neck, 500 mL round bottom flask containing a stir bar was added 2-methyl-8-acetamidoquinoline (5.69 g, 28.4 mmol) and platinum(IV) oxide (322 mg, 5 mol %). The flask was equipped with two Teflon cannulae: one for purging of the reaction flask with nitrogen gas and introduction of hydrogen, and the other leading to a flask connected to a bubbler. Trifluoroacetic acid (100 mL) was added to the reaction flask under an atmosphere of nitrogen. The stirred reaction mixture was flushed with nitrogen gas and warmed to 60° C. Hydrogen gas was bubbled through the stirred reaction for 3 h. The progress of the reaction was monitored by GC and/or TLC. The reaction mixture was cooled to room temperature, purged with nitrogen gas and the catalyst was filtered through a pad of Celite and washed with CH2Cl2 (100 mL). The solvent was removed in vacuo and the residue was basified with saturated NaOH (pH>14). The mixture was then extracted with CHCl3 (3×250 mL). The organic extracts were dried (MgSO4), filtered and concentrated. The crude material was purified by flash chromatography using 10% MeOH in EtOAc to provide the product (3.83 g, 66%) as a white solid. 1H NMR δ 1.57-1.66 (m, 1H), 1.77-1.86 (m, 2H), 2.02 (s, 3H), 2.44 (s, 3H), 2.43-2.57 (m, 1H), 2.68-2.73 (m, 2H), 4.67-4.74 (m, 1H), 6.79 (br s, 1H), 6.92 (d, 1H, J=8 Hz), 7.24 (d, 1H, J=8 Hz); 13C NMR δ 21.6, 25.4, 25.8, 29.6, 31.0, 53.0, 123.4, 131.4, 139.2, 155.9, 157.2, 172.2; ES-MS m/z: 227 (M+Na+).

1. additionTo a 3-neck, 500 mL round bottom flask containing a stir bar
2. customone for purging of the reaction flask with nitrogen gas and introduction of hydrogen
3. customthe other leading to a flask
4. additionTrifluoroacetic acid (100 mL) was added to the reaction flask under an atmosphere of nitrogen
5. customThe stirred reaction mixture
6. customwas flushed with nitrogen gas
7. customHydrogen gas was bubbled through the stirred reaction for 3 h
8. temperatureThe reaction mixture was cooled to room temperature
9. custompurged with nitrogen gas
10. filtrationthe catalyst was filtered through a pad of Celite
11. washwashed with CH2Cl2 (100 mL)
12. customThe solvent was removed in vacuo
13. extractionThe mixture was then extracted with CHCl3 (3×250 mL)
14. dry with materialThe organic extracts were dried (MgSO4)
15. filtrationfiltered
16. concentrationconcentrated
17. customThe crude material was purified by flash chromatography