4-Benzyloxy-1-methoxy-isoquinoline-3-carboxylic acid butyl ester → 4-Hydroxy-1-methoxy-isoquinoline-3-carboxylic acid butyl ester

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Reaction Steps

A mixture of 4-benzyloxy-1-methoxy-isoquinoline-3-carboxylic acid butyl ester (164 mg, 0.45 mmol), Pd/C (50 mg, 10 wt % Pd) and EtOAc (15 ml) was stirred under a H2-atmosphere at ambient pressure and temperature for 16 h. Then the mixture was filtered through a pad of celite. Celite and filter cake were washed thoroughly with EtOAc and the combined organic phases were concentrated in vacuo to give the title compound as a white solid (115 mg); 1H NMR (CDCl3): δ=11.48 (s, 1H), 8.27 to 8.32 (m, 1H), 8.17 to 8.21 (m, 1H), 7.65 to 7.78 (m, 2 H), 4.43 (t, 2 H), 4.10 (s, 3 H), 1.87 (m, 2 H), 1.54 (m, 2 H), 1.02 (t, 3 H).

Provenance & Evidence