2-Phenyl-2-propylsuccinic acid → 1-[3-(4-Oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-phenyl-3-propylpyrrolidine-2,5-dione

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 4-(3-aminobenzyl)-2H-phthalazin-1-one (0.1 g, 0.4 mmol; prepared in a manner similar to that described in Example 1) and 2-phenyl-2-propylsuccinic acid (0.094 g, 0.4 mmol) was heated at 200° C. for 1.5 hours then it was allowed to stand at ambient temperature for 18 hours. Methanol (1 ml) was added, the mixture was heated under reflux for 5 minutes, then it was filtered and the collected solid was washed with hot methanol (3 ml). The combined filtrate and washings were concentrated in vacuo and the residue was triturated with water (5 ml). The resulting solid was collected by filtration and dried in vacuo to give 1-[3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-3-phenyl-3-propylpyrrolidine-2,5-dione (0.061 g) as a beige solid, 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 0.95 (t, 3H) (CH3), 1.25 (m, 2H) (—CH2CH2CH3), 2.1 (m, 2H) (—CH2CH2CH3), 3.3 (d, 2H) (ring CH2), 4.4 (s, 2H) (ArCH2—), 7.2 (d, 1H) (ArH), 7.3–7.65 (m, 8H) (8×ArH), 7.85–8.1 (m, 3H) (3×ArH), 8.35 (d, 1H) (ArH), 12.7 (s, 1H) (CONH); m/z (M+H)+. 452, 93.6% purity.

Provenance & Evidence