Triethylamine → (4E)-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

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Reaction Steps

Using the procedure described for the preparation of (4Z)-6-bromo-4-{[(4-hydroxy-3-methoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione, 0.25 g (78% yield) of off-white solid is obtained from 0.2 g (0.98 mmol) of (4E)-4-(methoxymethylene)-isoquinoline-1,3(2H,4H)-dione and 0.2 g (1.08 mmol) of 4-methoxy]-3-hydroxyl-benzylamine hydrochloride, and 0.3 mL (2.94 mmol) of triethylamine: mp 192-193° C.; 1H NMR (DMSO-d6) δ 10.97 (s, 1H), 10.60 (m, 1H), 9.04 (s, 1H), 8.62 (d, J=9 Hz, 1H), 7.98 (d, J=6 Hz, 1H), 7.83 (d, J=6 Hz, 1H), 7.55 (t, J=6 Hz, 1H), 7.17 (t, J=6 Hz, 1H), 6.91 (d, J=6 Hz, 1H), 6.78 (m, 2H), 4.56 (d, J=4.5 Hz, 2H), 3.75 (s, 3H); MS (ESI) m/z 325.1 (M+H)+1.

Provenance & Evidence