[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[CH3:12][N:13]([CH3:19])[CH:14]1[CH2:18][CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:16]1[CH2:17][CH2:18][CH:14]([N:13]([CH3:19])[CH3:12])[CH2:15]1A mixture of 2-chloro-1-fluoro-4-nitrobenzene (4.79 g), dimethylpyrrolidin-3-ylamine (2.60 g), potassium carbonate (3.82 g) and DMF (35 mL) was stirred at room temperature for 4 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was extracted with hydrochloric acid (2 M), and the extract was basified with sodium hydroxide solution (2M). Extraction with ethyl acetate afforded an organic phase which was dried and concentrated. The product with the molecular weight of 269.73 (C12H16ClN3O2) was obtained in this way; MS (ESI): 270 (M+H+).
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