Reaktion #987002

Reaktionsgleichung

2-methyl-8-acetamidoquinoline

→

product

Ausbeute 66.0%

N-(2-methyl-5,6,7,8-tetrahydroquinolin-8-yl)acetamide

Ausbeute 66.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a 3-neck, 500 mL round bottom flask containing a stir bar
2. 2
   Sonstigeone for purging of the reaction flask with nitrogen gas and introduction of hydrogen
3. 3
   Sonstigethe other leading to a flask
4. 4
   workup.ADDITIONTrifluoroacetic acid (100 mL) was added to the reaction flask under an atmosphere of nitrogen
5. 5
   SonstigeThe stirred reaction mixture
6. 6
   Sonstigewas flushed with nitrogen gas
7. 7
   SonstigeHydrogen gas was bubbled through the stirred reaction for 3 h
8. 8
   TemperaturThe reaction mixture was cooled to room temperature
9. 9
   Sonstigepurged with nitrogen gas
10. 10
    Filtrationthe catalyst was filtered through a pad of Celite
11. 11
    Waschenwashed with CH2Cl2 (100 mL)
12. 12
    SonstigeThe solvent was removed in vacuo
13. 13
    ExtraktionThe mixture was then extracted with CHCl3 (3×250 mL)
14. 14
    TrocknenThe organic extracts were dried (MgSO4)
15. 15
    Filtrationfiltered
16. 16
    Einengenconcentrated
17. 17
    SonstigeThe crude material was purified by flash chromatography

Vorschrift

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+).

Quelle