[Cl:1][C:2]1[CH:12]=[CH:11]C(N)=[CH:9][C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].CI.O.[CH3:23][N:24]([CH:26]=O)[CH3:25]>>[CH2:7]([NH:6][C:4](=[O:5])[C:3]1[CH:9]=[C:26]([N:24]([CH3:23])[CH3:25])[CH:11]=[CH:12][C:2]=1[Cl:1])[CH3:8]A mixture of the above amine (3 g, 0.015 mol), potassium carbonate (3.8 g, 0.028 mol) and MeI (1.4 mL, 0.022 mol) in DMF stirred at RT overnight. The reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and brine, dried (MgSO4) and concentrated to give an oil. Purification by flash chromatography (0-50% ethyl acetate/hexanes) gave N-ethyl 2-chloro-5-(dimethylamino)benzamide as a yellow solid in 29% yield.
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