Dimethyl(methylene)ammounium iodide → 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide
Reaction equation
[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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Methyl indole-4-carboxylate (7.0 g, 40 mmol) and Eschenmoser's salt (N,N-dimethylnethyleneammonium 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.
Workup
- concentrationthe reaction mixture is concentrated in vacuo
- customThe resulting solid is triturated with ethyl acetate
- filtrationfiltered
- customdried in vacuo
Sources & evidence
- ORD record
- ord-3d8d5460c30f41d1a934edf62f31f4ee
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07208505B2
Reaction notes
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