Sodium Hydroxide → 2-Methoxy-1,8-naphthyridine-3-carboxylic acid

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Reaction Steps

Methyl 2-methoxy-1,8-naphthyridine-3-carboxylate (87.0 mg, 0.40 mmol) was dissolved in MeOH. NaOH (1.2 ml, 1M aqueous solution) was added to the solution and the mixture stirred at room temperature for 18 h. The organic solvent was removed under reduced pressure. The remaining aqueous residue was treated with HCl (1M aqueous solution) until slightly acidic and the product extracted with EtOAc. The combined organic phases were dried over MgSO4, filtered and concentrated yielding 2-methoxy-1,8-naphthyridine-3-carboxylic acid which was coupled without further purification to 3-(trifluoromethyl)benzylamine using the general amide coupling procedure. The crude product was purified by flash chromatography, CH2Cl2/MeOH 96:4, yielding 124 mg (86%) of the title compound.

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