[N+:1]([C:4]1[CH:5]=[C:6]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])[C:7](=[CH:15][CH:16]=1)[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])([O-])=O.Cl.O.[OH-].[Na+]>C1C=CC=CC=1.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])[C:7](=[CH:15][CH:16]=1)[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9]
Compound 403 (1.5 g, 4.6 mmol) was dissolved in 230 ml of benzene and then 2.8 g of purified zinc dust was added. Concentrated hydrochloric acid (8.2 ml) was added in portions. After 15 minutes of stirring at room temperature, another 2.8 g of zinc dust was added and the mixture was stirred at room temperature for 12 hours. Then 280 ml of water was added to the reaction mixture and the mixture was neutralized with 1N NaOH solution. The mixture was transferred to a separatory funnel and the benzene layer was removed. The aqueous layer was extracted with benzene. The combined benzene extracts were washed with water and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was purified by silica gel column chromatography (n-hexane: acetic acid =10:1) to give 980 mg (89.6%) of di-n-butyl 4-aminophthalate (compound 404).
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