Dimethyl(methylene)ammounium iodide → 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide
反応式
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[CH3:14][N+:15]([CH3:17])=[CH2:16].[I-:18]>C(O)(=O)C>[IH:18].[CH3:13][O:12][C:10]([C:5]1[C:4]2[C:3]([CH2:14][N:15]([CH3:17])[CH3:16])=[CH:2][NH:1][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:11]参加物
4
反応条件
- 温度
- 65 °C
実験手順
Methyl indole-4-carboxylate (7.0 g, 40 mmol) and Eschenmoser's salt (N,N-dimethylmethyleneammonium iodide; 7.8 g, 42 mmol) are combined in 130 ml of acetic acid. After heating at 65° C. for 2 hours, the reaction mixture is concentrated in vacuo. The resulting solid is triturated with ethyl acetate, filtered and dried in vacuo to give 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide in quantitative yield.