2-phenyl-3H-phthalazine-1,4-dione synthesis
- Product Name:2-phenyl-3H-phthalazine-1,4-dione
- CAS Number:5439-98-5
- Molecular formula:C14H10N2O2
- Molecular Weight:238.24
Yield:5439-98-5 93%
Reaction Conditions:
with hydrogenchloride in water; for 15 h;Reflux;
Steps:
1 2-Phenyl-2,3-dihydrophthalazine-1,4-dione (IRES-J019)
To a solution of phthalic anhydride (444 mg, 3.0 mmol, 1.0 eq) in 10% aq. HCl (30 mL) was added phenylhydrazine (0.35 mL, 3.6 mmol, 1.2 eq) dropwise and the reaction mixture was refluxed for 15 h. The resulting solid in reaction mixture was filtered off and washed with water and dried in vacuo. No further purification was needed to afford the desired product IRES-J019 (665 mg, 93%) as a pale peach solid: Rf = 0.25 (hexane/ethyl acetate, 2: 1, v/v); mp 216-218 °C; NMR (DMSO-d6, 500 MHz) δ 11.82 (s, 1H), 8.28 (dd, J= 7.5, 1.0 Hz, 1H), 8.00 (dd, J= 7.5, 1.0, 1H), 7.95 (td, J= 7.5, 1.0 Hz, 1H), 7.90 (td, J= 7.5, 1.0 Hz, 1H), 7.62 (d, J= 7.0 Hz, 2H), 7.47 (t, J= 7.5 Hz, 2H), 7.35 (t, J= 7.5 Hz, 1H) ppm; 13C NMR (DMSO-d6, 125 MHz) δ 157.8, 150.9, 142.2, 134.1, 133.0, 129.7, 128.9, 127.6, 127.3, 126.4, 125.1, 124.7 ppm; HRMS-ESI (m/z): [M+H]+ calcd for C14HuN202 239.08205; found, 239.08102. These data are in agreement with those previously reported.
References:
WO2017/192665,2017,A1 Location in patent:Page/Page column 38; 45
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