Water → (4Z)-5-bromo-4-[[(3-hydroxy-4-methoxyphenyl)methylamino]methylidene]isoquinoline-1,3-dione

Participants

Reaction Steps

A solution of 88.5 mg (0.468 mmol) of 3-hydroxy-4-methoxy-benzylamine hydrogen chloride in 1.8 mL of N,N-dimethylformamide (DMF) at RT under N2 is treated with 94.5 mg (0.936 mmol) of Et3N. (4E)-5-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (132 mg, 0.468 mmol) is added and the mixture is stirred for 3.5 h. Water is added and the product is collected, washed with H2O and Et2O and dried to give 163 mg (86%) of pale yellow amorphous solid: mp 204-206° C.; 1H NMR (DMSO-d6) δ 11.11 (s, 1H), 10.56 (m, 1H), 9.08 (s, 1H), 8.93 (d, 1H, J=13.6 Hz), 8.05 (d, 1H, J=6.9 Hz), 7.87 (d, 1H, J=6.9 Hz), 7.09 (m, 1H), 6.91 (d, 1H, J=8.07 Hz), 6.78 (m, 2H), 4.49 (d, 2H, J=5.37 Hz), 3.75 (s, 3H); HRMS (ESI) m/z calcd for C18H15BrN2O4 403.02880. found 403.02840 (M+H)+1.

Provenance & Evidence