Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-hydroxy-5-methoxybenzoate

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Reaction Steps

In a 1 l Schlenk flask filled with argon, methyl 4benzyloxy-5-methoxy-2-nitrobenzoate (11.60 g, 36.6 mmol) and palladium on charcoal (1.17 g, 10% Pd, 1.1 mmol Pd) were combined and tetrahydrofuran (250 mL) was added. The argon was replaced with hydrogen (1 bar), and the mixture was vigorously stirred at r.t. until completion of the reaction. The palladium was separated by filtration through a pad of celite and the solvent was removed to obtain methyl 2-amino-4-hydroxy-5-methoxybenzoate (6.56 g, 36.0 mmol, 98%) which was used without further purification LC/ESI-MS: m/z=166 [M−CH4O+H]+; Rt=2.17 min.

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