반응 #9929

반응 방정식

3-(3-ethoxy-4-methoxyphenyl)-3-(1,3-dioxo-2,3-dihydro-1H-benzo[f]isoindol-2-yl)propanoic acid

hydroxylamine hydrochloride

→

3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-(1,3-dioxo-2,3-dihydro-1H-benzo[f]-isoindol-2-yl)propionamide

수율 77.2%

용매

tetrahydrofuran

반응 조건

실험 절차

3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(1,3-dioxo-2,3-dihydro-1H-benzo[f]-isoindol-2-yl)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(1,3-dioxo-2,3-dihydro-1H-benzo[f]isoindol-2-yl)propanoic acid (2.00 g, 4.77 mmol), N,N′-carbonyldiimidazole (889 mg, 5.48 mmol) and hydroxylamine hydrochloride (419 mg, 6.03 mmol) in tetrahydrofuran (8 mL) to afford 3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-(1,3-dioxo-2,3-dihydro-1H-benzo[f]-isoindol-2-yl)propionamide as an off-white solid (1.6 g, 77% yield): mp, 197.0–199.0° C.; 1H NMR (DMSO-d6) δ 1.33 (t, J=7.0 Hz, 3H, CH3), 3.11–3.28 (m, 2H, CH2), 3.73 (s, 3H, CH3), 4.00 (q, J=7.0 Hz, 2H, CH2), 5.79 (t, J=7.8 Hz, 1H, NCH), 6.87–7.09 (m, 2H, Ar), 7.10 (br s, 1H, Ar), 7.74–7.78 (m, 2H, Ar), 8.23–8.27 (m, 2H, Ar), 8.49 (br s, 1H, Ar), 8.85 (br s, 1H, OH), 10.66 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 14.69, 34.27, 50.42, 55.45, 63.73, 111.73, 112.45, 119.82, 124.50, 127.04, 129.28, 130.26, 131.20, 135.05, 147.69, 148.58, 166.07, 167.30; Anal Calcd for C24H22N2O6: C, 66.35; H, 5.10; N, 6.45. Found: C, 66.22; H, 5.24; N, 6.08.

출처