HCID 10156578, compound → 3-Amino-6-hydroxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A solution of 4.7 g (12.0 mmol) of 3-amino-6-benzyloxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester and 2.0 g of 10% Pd/C in 40 mL of DMF and 100 mL of methanol is shaken on Parr shaker at 40 psi for 18 hours. The hydrogenation is repeated twice more to bring the reaction to completion. The catalyst is filtered through a pad of Celite, is washed with methanol and solvent is evaporated to yield a residue which is dissolved in methylene chloride. This is then filtered through a short pad of Magnesol and is washed with methylene chloride and ethyl acetate. The filtrate is evaporated to yield 3.4 g of 3-amino-6-hydroxy-7-methoxy-naphthalene-2-carboxylic acid tert-butyl ester as a yellow solid, mp 262-263° C.

Provenance & Evidence