Methyl 4-(benzyloxy)-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate → Methyl 4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate

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Reaction Steps

To a solution of methyl 4-(benzyloxy)-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate (200.0 mg, 0.47 mmol) in EtOAc (21 mL) was added a suspension of Pd/C (171.3 mg, 0.16 mmol, 10% by weight) in EtOH (21 mL). The resulting mixture was stirred at room temperature under a hydrogen atmosphere for 16 hours. The resulting suspension was filtered through a pad of celite. The filtrate was concentrated in vacuo and then purified by flash chromatography (0-30% EtOAc/CH2Cl2) to give the title compound in 120.0 mg. 1H NMR (CDCl3, 200 MHz): δ=11.63 (s, 1H), 8.51 (s, 1H), 8.13 (d, 1H, J=9.0 Hz), 7.30 (d, 2H, J=6.6 Hz), 7.06 (d, 1H, J=9.0 Hz), 6.94-6.82 (m, 3H), 4.39 (s, 2H), 4.04 (s, 3H), 3.80 (s, 3H).

Provenance & Evidence