反应 #40348

反应方程式

4-trifluoromethyl-6-nitroquinolinone

CsF

2-iodopropane

→

2-isopropoxyquinoline

收率 99.9%

6-Amino-2-isopropoxy-4-trifluoromethylquinoline

收率 99.9%

溶剂

DMF

反应条件

后处理

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

实验过程

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).

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