[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([Cl:12])=[C:7]([NH2:11])[CH:8]=2)[NH:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([Cl:12])=[C:7]([NH2:11])[CH:8]=2)[N:3]1[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]To a mixture of 2-oxo-5-amino-6-chloroindoline (3.2 g), potassium carbonate (4.8 g) and acetone (60 ml) was added dropwise ethyl chloroacetate (3.2 g) at ambient temperature. The reaction mixture was refluxed with stirring for 4 hours and then filtered under warm condition. The filter cake was washed with acetone. The combined filtrate and washings were concentrated under reduced pressure to give a residue, which was purified by a column chromatography on silica gel to give crystalline ethyl 2-oxo-5-amino-6-chloro-1-indolineacetate (0.9 g).
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