[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.[CH2:15]([NH:17][CH3:18])[CH3:16].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:15]([N:17]([CH3:18])[C:12]([C:4]1[CH:3]=[C:2]([OH:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[O:14])[CH3:16]
4-Hydroxyquinoline-2-carboxylic acid (1.00 g, 5.29 mmol) was dissolved in DMF (10 mL), and N-ethylmethylamine (91 μL, 10.6 mmol), WSC.HCl (2.03 g, 10.6 mmol), and HOBt.H2O (1.62 g, 10.6 mmol), were added thereto, and the mixture was stirred at room temperature for 3 hours. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=95/5) to give N-ethyl-4-hydroxy-N-methyl-quinoline-2-carboxamide (615 mg, 2.67 mmol, yield: 50%). Mass (m/e): 231 (M+H)+.
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