[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]#[N:13])[CH:3]=1.Cl.[NH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+].[C:23]([O:26][CH2:27][CH3:28])(=[O:25])[CH3:24]>C(O)(C)(C)C.O>[CH2:27]([O:26][C:23]([C:24]1[O:16][N:15]=[C:12]([C:4]2[CH:3]=[C:2]([OH:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=2)[N:13]=1)=[O:25])[CH3:28]
A mixed solution of 4-hydroxynaphthalene-2-carbonitrile (0.34 g), hydroxylamine hydrochloride (0.14 g) and potassium carbonate (0.30 g) in tert-butylalcohol (4.5 mL) and water (0.5 mL) was stirred at 80° C. for 6 hours. To the reaction mixture was added hydroxylamine hydrochloride (0.14 g), and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol). This compound (0.22 g) was dissolved in dichloromethane (5.3 mL). To the mixture were added ethyl oxalyl chloride (0.35 mL) and pyridine (0.52 mL), and the mixture was stirred at room temperature for 1.5 hours. To the reaction solution was added water, and the organic layer was washed with water and a saturated sodium hydrogen carbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate) to give the title compound (0.15 g).
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