C(=O)(O)[O-].[Na+].C(OCC)(=O)C.Cl.[NH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[Cl:25][CH2:26][C:27](Cl)=[O:28]>O>[Cl:25][CH2:26][C:27]([NH:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24])=[O:28]To a stirred solution of sodium bicarbonate (4.0 g) in water (50 ml) layered with ethyl acetate (200 ml) was added solid 2-amino-3,4-dihydronaphthalen-1(2H)-one hydrochloride (4.0 g, 2 mmol). After the solid had dissolved chloroacetylchloride (1.6 ml, 2 mmol) was added dropwise over 10 minutes. After stirring for 1 hr, the ethyl acetate layer was separated, washed with brine and dried over Na2SO4. Evaporation afforded 2.7 g (57%) of a dark solid; m.p. 118°-122° C. The product was purified by chromatography on silica using ethyl acetate: hexane (1:1 v/v) to elute, m.p. 121°-123° C.
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