[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:14]1([CH3:23])[CH:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1.[OH-].[Na+].C(OCC)(=O)C>C1C=CC=CC=1.O>[CH3:23][C:14]1[CH:19]=[CH:18][C:17]([C:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=2)=[O:21])=[CH:16][CH:15]=110 g of ethyl 4-aminophenylacetate was dissolved in 120 ml of benzene and to this was further added 25 ml of water. To this solution were added dropwise a solution of 8.6 g of p-toluoyl chloride dissolved in 20 ml of benzene and a solution of 2.4 g of 93% NaOH dissolved in 25 ml of water simultaneously under stirring over 15 minutes. After completion of the dropwise addition, the solution was stirred for 3 hours and allowed to stand overnight. After adding 200 ml of ethyl acetate, the oil layer was separated, washed with 1N-HCl solution and with a saturated solution of sodium chloride, and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was recrystallized from benzene-n-hexane to give 12 g of ethyl 4-(4-methylbenzoylamino)phenylacetate.
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