[F:1][C:2]1[CH:11]=[C:10]([N:12]=[C:13]=[S:14])[C:9]([CH3:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:16]([NH2:19])[CH2:17][NH2:18]>C1(C)C=CC=CC=1>[NH2:18][CH2:17][CH2:16][NH:19][C:13](=[S:14])[NH:12][C:10]1[C:9]([CH3:15])=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([F:1])[CH:11]=1A solution of 5-fluoro-7-isothiocyanato-8-methylquinoline (0.38 g) in toluene (40 mL) is added dropwise to a solution of ethylenediamine (0.78 g) in toluene (40 mL). A white precipitate is observed after the reaction stirs for 10 minutes at room temperature. The precipitate is filtered and dried in vacuo to afford 7-[N'-(2-aminoethyl)thioureido]-5-fluoro-8-methylquinoline as a white solid.
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