Reacción #9944

Ecuación de reacción

3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid

carbonyldiimidazole

N-methyl-hydroxylamine hydrochloride

→

N-Hydroxy-3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propionamide

N-hydroxy-N-methyl-3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propionamide

Rendimiento 120.8%

Disolventes

tetrahydrofuran

Condiciones de reacción

Procedimiento

N-Hydroxy-3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propanoic acid (1.0 g, 2.8 mmol), carbonyldiimidazole (500 mg, 3.1 mmol) and N-methyl-hydroxylamine hydrochloride (300 mg, 3.5 mmol) in tetrahydrofuran (10 mL) to afford N-hydroxy-N-methyl-3-(3-ethoxy-4-methoxyphenyl)-3-(1-oxoisoindolinyl)propionamide as a white solid (650 mg, 61% yield): mp, 122.0–124.5° C.; 1H NMR (CDCl3) δ 1.43 (t, J=7.0 Hz, 3H, CH3), 3.14 (s, 3H, NCH3), 3.37–3.48 (m, 2H, CH2), 3.86 (s, 3H, CH3), 4.02 (q, J=7.0 Hz, 2H, CH2), 4.11 (d, J=17.2 Hz, NCHH), 4.51 (d, J=17.2 Hz, 1H, NCHH), 5.95 (dd, J=6.5, 10.9 Hz, 1H, NCH), 6.83–6.97 (m, 3H, Ar), 7.34–7.55 (m, 3H, Ar), 7.81 (d, J=7.1 Hz, 1H, Ar), 9.44 (br s, 1H, OH); 13C NMR (DMSO-d6) δ 14.71, 36.04, 38.11, 48.14, 52.36, 55.95, 64.52, 111.42, 112.42, 119.45, 122.95, 123.63, 128.06, 130.57, 131.88, 141.72, 148.65, 149.18, 170.00, 170.17; Anal Calcd for C21H24N2O5: C, 65.61; H, 6.29; N, 7.29. Found: C, 65.56; H, 6.26; N, 7.09.

Fuente