2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → N-[2-(2-Diethylaminoethylamino)-5-nitro-phenyl]-2-(4-ethoxyphenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

N1-(2-Diethylamino-ethyl)-4-nitro-benzene-1,2-diamine 4a (0.47 g, 1.863 mmol) was dissolved in anhydrous dichloromethane (110 mL) in a small, argon purged flask fitted with an condenser and magnetic stirbar. (4-Ethoxy-phenyl)-acetic acid 5 (0.352 g, 1.956 mmol) followed by 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.552 g, 2.235 mmol) are added quickly as solids and resulting solution heated in an oil bath at 35° C. for 18 hours. After cooling to room temperature the solvent was removed under reduced pressure and the resulting residue partitioned between H2O and chloroform and 3M ammonium hydroxide solution added to adjust pH to 11-12. 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 solid. Recrystallization of the crude solid from ethyl acetate yielded a yellow powder 6a N-[2-(2-Diethylamino-ethylamino)-5-nitro-phenyl]-2-(4-ethoxy-phenyl)-acetamide. Yield: 0.305 grams (39.5%). 1H NMR (DMSO) δ: 0.94 (t, 6H, J=7.1), 1.31 (t, 3H, J=6.9), 2.50 (m, 4H), 2.59 (t, 2H, J=6.5), 3.26 (m, 2H), 3.55 (s, 2H), 4.02 (q, 2H, J=6.9), 6.21 (br s, 1H), 6.75 (d, 1H, J=9.9), 6.87 (d, 2H, J=8.4), 7.24 (d, 2H, J=8.4), 7.97 (m, 2H), 9.54 (br s, 1H); MS (ESI): 415 (MH+, 100%)

Provenance & Evidence