Propionamide → N-[4-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-5,6-dihydro-isoquinolin-8-yl]-propionamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred suspension of 1-methyl-6-(8-oxo-5,6,7,8-tetrahydro-isoquinolin-4-yl)-3,4-dihydro-1H-quinolin-2-one) (919 mg, 3 mmol, example 70) and propionic acid amide (658 mg, 9 mmol) in trifluorotoluene (30 mL) was added trifluoromethane sulfonic acid (585 mg, 3.9 mmol) and the reaction was stirred at 102° C. After 4 h, a solution of trifluoromethane sulfonic acid (158 mg, 1.05 mmol) in trifluorotoluene (5 mL) was added and the reaction mixture stirred for further 8 h. After this time, propionic acid amide (219 mg, 3 mmol) and a solution of trifluoromethane sulfonic acid (158 mg, 1.05 mmol) in trifluorotoluene (5 mL) were added and the stirring continued at 102° C. over night. The reaction mixture was allowed to cool down to room temperature and aq. NaOH 2 M (30 mL) was added. The resulting mixture was extracted with dichloromethane (3×) and the organic phases washed with aq. sat. NaCl solution (2×). The combined organic phases were dried over Na2SO4, filtered and evaporated. Crystallization of the crude product (dichloromethane/ethyl acetate/heptane) afforded the title compound (915 mg, 84% yield) as off-white crystals. MS: 362.2 (M+H+).

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