(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione → HCID 178518256, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.00 g (7.09 mmol) of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione and 1.24 g (7.80 mmol) of 4-(1H-Imidazol-4-yl)aniline in 22 mL of N,N-dimethylformamide (DMF) is heated at 120° C. for 1.25 h. The chilled reaction mixture is filtered and the insoluble material is washed with N,N-dimethylformamide (DMF) and Et2O. In order to remove residual N,N-dimethylformamide (DMF), the solid is boiled with MeOH (2×), washed with Et2O and dried in vacuo. The yield is 2.10 g (72%) of yellow-brown crystals: mp >300° C. (dec); 1H NMR (DMSO-d6) δ 12.6 (d, 1H, J=12.7 Hz), 12.2 (s, 1H), 11.4 (s, 1H), 8.98 (d, 1H, J=12.7 Hz), 8.49 (s, 1H), 7.86 (m, 3H), 7.67 (m, 4H), 7.41 (d, 1H, J=8.34 Hz); HRMS (ESI) m/e calcd for C19H13BrN4O2 409.02947. found 409.02902 (M+H)+1.

Provenance & Evidence