反応 #40348

反応方程式

4-trifluoromethyl-6-nitroquinolinone

CsF

2-iodopropane

→

2-isopropoxyquinoline

収率 99.9%

6-Amino-2-isopropoxy-4-trifluoromethylquinoline

収率 99.9%

溶媒

DMF

反応条件

後処理

1. 1
   その他The reaction mixture was quenched with H2O (100 mL)
2. 2
   抽出extracted with EtOAc (3×200 mL)
3. 3
   洗浄The combined EtOAc extracts were washed with saturated aqueous NH4Cl solution (300 mL), H2O (300 mL) and brine (300 mL)
4. 4
   乾燥Dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was purified by flash column chromatography (SiO2, 5×20 cm, 2% EtOAc in hexane as eluent)

実験手順

In a 250-mL r.b. flask, a solution of 4-trifluoromethyl-6-nitroquinolinone (structure 1 of Scheme I) (3.78 g, 14.6 mmol) in DMF (75 mL) was treated with CsF (12.41 g, 73 mmol, 5.0 equiv.) and 2-iodopropane (11.09 g, 73 mmol, 5.0 equiv). The reaction mixture was stirred at room temperature (rt) for 18 h. The reaction mixture was quenched with H2O (100 mL) and extracted with EtOAc (3×200 mL). The combined EtOAc extracts were washed with saturated aqueous NH4Cl solution (300 mL), H2O (300 mL) and brine (300 mL). Dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 5×20 cm, 2% EtOAc in hexane as eluent) to afford 3.94 g (90%) of the 2-isopropoxyquinoline as a white solid. Rf 0.81 (SiO2, 10% EtOAc-hexane). 1H NMR (400 MHz, CDCl3) 8.93 (s, 1H), 8.47 (dd, 1H, J=9.2, 2.5), 7.98 (d, 1H, J=9.2), 7.32 (s, 1H), 5.62 (septet, 1H, J=6.2), 1.45 (d, 1H, J=6.2).

出典