O-Xylene → Phthalazine

Participants

Reaction Steps

1,1′-Carbonyldiimidazole (0.917 g, 5.65 mmol) was added to a stirred solution of 3-furoic acid (0.634 g, 5.65 mmol) in DMF (30 ml). The solution was stirred for 2 h before adding the preceding hydrazine (1.19 g, 5.14 mmol) and triethylamine (0.71 ml, 5.14 mmol) and triethylamine (0.71 ml, 5.14 mmol). After 18 h at room temperature, the solvent was evaporated in vacuo and water added to the residue. The resultant precipitate was collected by filtration, washed with water and hexane and dried in vacuo to give the ketohydrazine (0.66 g, 45%), MS (ES+) m/e 289 [MH]+. A solution of the ketohydrazine (0.66 g, 2.3 mmol) and triethylamine hydrochloride (0.07 g, 0.5 mmol) in xylene (40 ml) was heated at reflux for 18 h. The solution was cooled to room temperature and the solvent evaporated in vacuo. Diethyl ether was added to the residue and the resulting solid collected by filtration, washed with diethyl ether and dried in vacuo to give the title-phthalazine (0.46 g, 74%), 1H NMR (250 MHz, CDCl3) δ 7.32 (1H, d, J=1.8 Hz, Ar—H), 7.62 (1H, d, J=1.4 Hz. Ar—H), 7.90 (1H, m, Ar—H), 8.04 (1H, t, J=7.6 Hz, Ar—H), 8.31 (1H, d, J=8.2 Hz, Ar—H), 8.58 (1H, s, Ar—H), 8.75 (1H, d, Ar—H); MS (ES+) m/e 271 [MH]+.

Provenance & Evidence