[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][CH:11]2[CH2:13][CH2:12]2)=C([CH:9]=1)C#N.[OH-:14].[K+].Cl.C1(C)C=CC=CC=1.[CH3:24][CH2:25][OH:26]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:10][CH:11]2[CH2:13][CH2:12]2)=[C:24]([CH:9]=1)[C:25]([OH:14])=[O:26]5-Chloro-2-(cyclopropylamino)benzonitrile (4.66 g) was dissolved in a solution of KOH (4.75 g, 3.5 eq) in EtOH (12 mL) and water (2.5 mL). The solution was refluxed for 24 h, cooled, and acidified with concentrated HCl. The precipitate was filtered, washed with water, and dried by multiple concentrations from toluene delivering pure product (4.70 g, 92% yield). 1H-NMR (400 MHz, DMSO-d6) δ 7.88 (bs, 1H), 7.70 (d, 1H), 7.42 (dd, 1H), 7.09 (d, 1H), 2.47 (m, 1H), 0.78 (m, 2H), 0.45 (m, 2H).
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