2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → N-(2-Amino-5-nitro-phenyl)-2-(4-ethoxy-phenyl)-acetamide

関与物質

反応条件

反応手順

4-Nitro-benzene-1,2-diamine 40 (1.00 g, 6.53 mmol) was dissolved in anhydrous dimethylformamide (20 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (1.53 g, 8.49 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (2.099 g, 8.49 mmol) are added quickly as solids and resulting solution heated in an oil bath at 100° C. for 17 hours. After cooling to room temperature the solution was diluted with ice cold H2O (25 mL) resulting in the formation of a yellow precipitate that was collected on a sintered glass funnel and washed with H2O. The solid was slurried in boiling ethanol, filtered and dried to yield solid 41 N-(2-Amino-5-nitro-phenyl)-2-(4-ethoxy-phenyl)-acetamide Yield: 1.31 grams (67.5%). 1H NMR (DMSO) δ: 1.31 (t, 3H, J=6.9), 3.61 (s, 2H), 4.00 (q, 2H, J=6.9), 6.50 (br s, 2H, exchange w. D2O), 6.75 (d, 1H, J=9.0), 6.87 (d, 2H, J=8.4), 7.25 (d, 2H, J=8.7), 7.84 (dd, 1H, J=9.0, 2.7), 8.20 (d, 1H, J=2.7), 9.37 (br s, 1H, exchange w. D2O); MS (APCI+): 316 (MH+, 10%), 298 (MH+-H2O, 100%).

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