[NH:1]1[C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][C:5]=2[C:4](=[O:15])OC1=O)[CH:12]=[CH:11][CH:10]=[CH:9]3.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1>C1(C)C(C)=CC=CC=1.CN(C)C1C=CN=CC=1>[NH2:1][C:6]1[C:5]([C:4]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=2)=[O:15])=[CH:14][C:13]2[C:8]([CH:7]=1)=[CH:9][CH:10]=[CH:11][CH:12]=2A suspension of 2H-naphth[2,3-d][1,3]oxazine-2,4(1H)-dione (216 mg) and 2-amino-5-chloropyridine (202 mg) in xylene (5 ml) is stirred at 150° C. for 13 hours, and thereto added 4-dimethylaminopyridine (14.4 mg) and the mixture is stirred at 150° C. for another 3 hours. The reaction solution is concentrated under reduced pressure and the resulting residue is suspended in ethyl acetate, and filtered to remove insoluble materials. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give 3-amino-N-(5-chloropyridin-2-yl)-2-naphthamide (24 mg).
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