Hydrochloric Acid → 6,8-Dimethoxyquinoline

Participants

Reaction Conditions

Reaction Steps

2,4-Dimethoxyaniline (20.0 g, 131 mmol), 8.70 mL (7.30 g, 131 mmol) acrolein and 500 mL 1 N HCl are refluxed for 30 min. The reaction mixture is cooled to 23° C., poured into 200 mL of vigorously stirring EtOAc, and neutralized with 10N NaOH. The resulting bi-phasic solution is stirred for 30 min and filtered through celite. The layers are separated, and the aqueous layer is extracted with 3×300 mL EtOAc. 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 on SiO2, eluting with 4/1 EtOAc/hexanes containing 10% MeOH, gives 6.40 g (33.8 mmol, a 26% yield) of the title compound as an off-white solid. MS (ES) m/z 190 (MH)+.

Provenance & Evidence