[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:20][CH2:21][N:22]([CH3:24])[CH3:23]>CC(C)=O>[CH3:23][N:22]([CH3:24])[CH2:21][CH2:20][O:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]To a solution of 2-hydroxy-4-methoxy-benzonitrile (200 mg, 1.341 mmol) in acetone (5 mL) were added cesium carbonate (1.312 g, 4.023 mmol) and (2-chloroethyl)-dimethylamine hydrochloride (390 mg, 2.682 mmol). The resulting mixture was heated at 60° C. for overnight. The solid was filtered off and washed with methylene chloride (6×10 mL). The filtrate was washed with sodium bicarbonate solution, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0-5% methanol in methylene chloride yielded 2-(2-dimethylamino-ethoxy)-4-methoxy-benzonitrile as a pale-yellow oil (210 mg, 71%).
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