N-Aminophthalimide → 2-[2-(2-chloro-4-methoxyphenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2-chloro-4-methoxyphenyl)-3-methyl-4-oxobutanal (6.40 g, 27.0 mmol) and N-aminophthalimide (5.32 g, 29.0 mmol) in HCl (5N, 3.90 mL) and dioxane (100 mL) was heated at 100° C. for 1 h. After cooling down to room temperature, the mixture was concentrated in vacuo and the residue was recrystalized from CH2Cl2/hepatene to give 9.22 g (95%) of pink solid as the title compound: mp 202.0–208.5° C.; 1H NMR (400 MHz, Acetone-d6) δ 7.95–7.86 (m, 4H), 7.17 (d, J=8.6 Hz, 1H), 7.01 (d, J=3.1 Hz, 1H), 6.99 (d, J=2.6 Hz, 1H), 6.82 (dd, J=8.6, 2.6 Hz, 1H), 6.20 (d, J=3.1 Hz, 1H), 3.77 (s, 3H), 1.98 (s, 3H); IR (diffuse reflectance) 2072, 2014, 1981, 1906, 1747, 1463, 1293, 1275, 1214, 1047, 881, 820, 719, 712, 705 cm−1; HRMS (FAB) calcd for C20H15N2O3Cl+H 367.0849. found 367.0832. Anal. Calcd for C20H15N2O3Cl: C, 65.49; H, 4.12; N, 7.64. Found: C, 65.16; H, 3.99; N, 7.58.

Provenance & Evidence