Reaktion #2073679

Reaktionsgleichung

tert-butyl (2-{[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}ethoxy)acetate

ammonia

→

tert-butyl (2-{[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)-6-quinolinyl]oxy}ethoxy)acetate

Ausbeute 66.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

To a mixture of tert-butyl (2-{[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}ethoxy)acetate (0.9 g, 1.9 mmol), 25% aqueous ammonia (5 ml) and methanol (50 ml) was added Raney-nickel (1 ml), and the mixture was stirred under a hydrogen atmosphere at 0.5 MPa, room temperature for 5 hrs. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl (2-{[3-(aminomethyl)-2-isobutyl-4-(4-methylphenyl)-6-quinolinyl]oxy}ethoxy)acetate as an oil (0.6 g). The oil and p-toluenesulfonic acid monohydrate (0.23 g, 1.2 mmol) were dissolved in ethanol (50 ml) and concentrated under reduced pressure. The residue was crystallized from diethyl ether and recrystallized from methanol-diethyl ether to give the title compound (0.7 g, yield 58%) as crystals.

Quelle