Benzoyl chloride → N-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzamide

Participants

Reaction Steps

Triethylamine (5.9 ml, 42 mmol) was added dropwise to a stirred suspension of 4-aminomethyl-2H-phthalazin-1-one hydrochloride (Geterotsikl. Soedin, 1972, (9), 15) (3.00 g, 14.2 mmol) in DMF (150 ml) at room temperature under nitrogen. The mixture was stirred for 1.5 h before the addition of benzoyl chloride (2.5 ml, 22 mmol) and then stirred at room temperature overnight. The reaction mixture was filtered and water added to the filtrate to form a solid. The mixture was cooled and the solid collected by filtration, washed successively with diethyl ether and isohexane, and dried in vacuo to give the title-compound (3.18 g, 80%), 1H NMR (360 MHZ, d6-DMSO) δ 4.81 (2H, d, J=5.6 Hz, CH2), 7.43-7.53 (3H, m, 3 of Ar—H), 7.83-7.96 (4H, m, 4 of Ar—H), 8.08 (1H, d, J=7.9 Hz, Ar—H), 8.28 (1H, dd, J=7.8 and 1.2 Hz, Ar—H), 8.98 (1H, br s, NH), 12.62 (1H, s NH).

Provenance & Evidence