반응 #40348

반응 방정식

4-trifluoromethyl-6-nitroquinolinone

CsF

2-iodopropane

→

2-isopropoxyquinoline

수율 99.9%

6-Amino-2-isopropoxy-4-trifluoromethylquinoline

수율 99.9%

용매

DMF

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with H2O (100 mL)
2. 2
   추출extracted with EtOAc (3×200 mL)
3. 3
   세척The combined EtOAc extracts were washed with saturated aqueous NH4Cl solution (300 mL), H2O (300 mL) and brine (300 mL)
4. 4
   건조Dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was purified by flash column chromatography (SiO2, 5×20 cm, 2% EtOAc in hexane as eluent)

실험 절차

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).

출처