Reacción #331394

Ecuación de reacción

carbonate

Acetophenone

1-(2-amino-4-chlorophenyl)ethanone

→

title compound

7-Chloro-4-methyl-2-phenylquinoline

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathen cooled to rt
2. 2
   Otropartitioned between EtOAc and H2O
3. 3
   ExtracciónThe aq layer was extracted with EtOAc
4. 4
   SecadoThe combined organics were dried (Na2SO4)
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroPurification by flash chromatography on SiO2 (70 g, EtOAc in hexanes 0:100->1:40->1:30)
7. 7
   Otroafforded a lightly colored oil
8. 8
   OtroThe resins were removed by filtration through Celite
9. 9
   LavadoThe residue and Celite were rinsed with DCM multiple times
10. 10
    ConcentraciónThe filtrate was concentrated under reduced pressure

Procedimiento

Acetophenone (0.66 mL, 5.69 mmol) was added to 1-(2-amino-4-chlorophenyl)ethanone (0.868 g, 5.69 mmol) and [Hbim]BF4 (1.50 g, 7.08 mmol) under Ar. The reaction mixture was heated at 100° C. for 57 h then cooled to rt and partitioned between EtOAc and H2O. The aq layer was extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography on SiO2 (70 g, EtOAc in hexanes 0:100->1:40->1:30) afforded a lightly colored oil. The material was dissolved in DCM (100 mL) and stirred with PS-Ts-NHNH2 (2.07 g, 2.87 mmol/g, 5.94 mmol) for 2.5 d at rt and then with MP-carbonate (˜0.25 g, 2.74 mmol/g, 0.68 mmol) for 4 h. The resins were removed by filtration through Celite. The residue and Celite were rinsed with DCM multiple times. The filtrate was concentrated under reduced pressure to provide the title compound as a light yellow oil; 1H NMR (400 MHz, CDCl3) δ 8.18-8.12 (m, 3H), 7.92 (d, J=8.4 Hz, 1H), 7.71 (d, J=0.8 Hz, 1H), 7.54-7.46 (m, 4H), 2.75 (s, 3H); MS (ES+): m/z 254.24 (35) [MH+]; HPLC: tR=3.82 min (OpenLynx, nonpolar—5 min).

Fuente