2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 59799751, compound

Participants

Reaction Steps

N1-(1-Methyl-piperidin-4-yl)-4-nitro-benzene-1,2-diamine 52 (0.330 g, 1.318 mmol) was dissolved in anhydrous dichloromethane (15 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (0.249 g, 1.384 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.391 g, 1.582 mmol) are added quickly as solids and resulting solution heated to reflux for 14 hours. After cooling to room temperature the solvent was removed under reduced pressure and the resulting residue partitioned between H2O and chloroform and 2M ammonium hydroxide solution added to adjust pH to 10. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with chloroform and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated to afford crude. Recrystallization of the crude from ethyl acetate yielded a yellow solid 53 2-(4-Ethoxy-phenyl)-N-[2-(1-methyl-piperidin-4-ylamino)-5-nitro-phenyl]-acetamide. Yield: 0.200 grams (36.8%). 1H NMR (DMSO) δ: 1.31 (t, 3H, J=6.9), 1.41-1.56 (m, 2H), 1.86-1.89 (m, 2H), 1.99-2.07 (m, 2H), 2.17 (s, 3H), 2.69-2.73 (m, 2H), 3.37-3.45 (m, 1H), 3.61 (s, 2H), 4.00 (q, 2H, J=7.0), 5.89 (d, 1H, J=7.5), 6.81 (d, 1H, J=9.3), 6.89 (d, 2H, J=8.4), 7.26 (d, 2H, J=8.3), 7.92 (dd, 1H, J=9.3, 2.3), 8.10 (d, 1H, J=2.3), 9.47 (br s, 1H); MS (ESI): 413 (MH+, 100%).

Provenance & Evidence