[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[K+].C(O)C.Cl>O>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1A mixture of 4.5 g. of ethyl 4-{[3-(4-chlorophenoxy)propyl]amino}benzoate 4.5 g. of potassium hydroxide and 100 ml. of 95% ethanol is refluxed for 3 hours. The solution is acidified with hydrochloric acid and the mixture is diluted with 100 ml. of water to give 3.7 g. of solid. Recrystallization by dissolving in a mixture of chloroform-ethyl acetate and diluting with hexane gives 3.3 g. of product as off-white crystals, m.p. 180°-181° C.
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