5-Methylsalicylic acid → N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-hydroxy-5-methylbenzamide

Beteiligte Stoffe

Reaktionsschritte

A mixture of 5-methylsalicylic acid (0.691 g, 4.5 mmol), 4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butan-1-amine (1.0 g, 3.8 mmol), N,N′-Dicyclohexylcarbodiimide (DCC) (0.94 g, 4.5 mmol) and 1-Hydroxybenzotriazole hydrate (HOBOt) (0.61 g, 4.5 mmol) in dichloromethane (20 mL) was stirred overnight under an atmosphere of nitrogen. The reaction mixture was washed with saturated sodium bicarbonate solution (3×10 mL). The organic solution was dried over Na2SO4 and volatiles were removed under reduced pressure. The residue was purified by silica gel column with methanol/ether (5/95, v/v) as the mobile phase to afford 4a as a viscous oil (1.39 g; 93%). 1H NMR (300 MHz, CDCl3): 1.70-1.78 (m, 4H), 2.09 (s, 3H), 2.50-2.60 (m, 2H), 2.68-2.76 (m, 2H), 2.78-2.88 (m, 2H), 3.44-3.60 (m, 4H), 3.82 (s, 3H), 3.83 (s, 3H), 6.48 (s, 1H), 6.58 (s, 1H), 6.83-6.87 (d, 1H), 7.00-7.04 (m, 1H), 7.10-7.16 (m, 1H), 7.70-7.90 (s, 1H).

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