Reaktion #72677

Reaktionsgleichung

Methyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate

4-methoxybenzylamine

→

methyl 4-(4-methoxybenzylamino)-2-oxo-1,2-dihydroquinoline-3-carboxylate

Lösungsmittel

—

hexanes

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   FiltrationThe resultant precipitate was collected by filtration
3. 3
   Sonstigefurther chromatographed on silica gel (0% to 20% MeOH in dichloromethane)

Vorschrift

Methyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 69) (0.928 g, 3.91 mmol) was dissolved in DMF (6 mL), and 4-methoxybenzylamine (1.14 mL, 8.78 mmol) was added. The reaction was heated at 90° C. for 30 minutes, then cooled to room temperature and poured into a stirred mixture of 50 mL hexanes and 100 mL ice water. The resultant precipitate was collected by filtration and further chromatographed on silica gel (0% to 20% MeOH in dichloromethane) to give methyl 4-(4-methoxybenzylamino)-2-oxo-1,2-dihydroquinoline-3-carboxylate as an off white solid (0.841 g, 64%). MS 339 (MH+).

Quelle