[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:23])[C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(O)C.[OH-].[K+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:23])[C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1A 1.80 g. portion of 4-[[3-(p-chlorophenyl)propyl]methylamino]benzoic acid, ethyl ester is dissolved in 15 ml. of 95% ethanol. A 1 g. portion of potassium hydroxide is added, and the mixture is refluxed overnight. The solution is poured into 30 ml. of water, the pH is adjusted to 6 using 37% hydrochloric acid, and the solid is collected and dried. This solid is dissolved in benzene, filtered, and evaporated, giving 750 mg. of the desired product.
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