Glycerol → 6-Methoxy-8-nitroquinoline

Participants

Reaction Conditions

Reaction Steps

4-Methoxy-2-nitroaniline (20.0 g, 119 mmol), 34.0 g (369 mmol) glycerol, 24.0 g (107 mmol) 3-nitrobenzensulfonic acid sodium salt, 25 mL H2O and 34 mL H2SO4 are refluxed for 12 h. The reaction mixture is cooled to 45° C., poured into 1 L of cold H2O and vigorously stirred with 500 mL of CH2Cl2 for 30 min. The resulting bi-phasic solution is filtered through celite, and the aqueous layer is extracted with 3×300 mL CH2Cl2. The combined organics are washed with 1×400 mL H2O, 1×400 mL brine, dried over MgSO4, filtered, and the volatiles are evaporated. Flash chromatography of the crude product on SiO2 gel, eluting with hexanes/EtOAc (4/1), gives 10.0 g (49.0 mmol, a 42% yield) of the title compound as a tan solid. MS (ES) m/z 205 (MH)+.

Provenance & Evidence