Methyl iodide → 5-[2-(2,5-Dimethoxyphenyl)ethyl]-2-methylamino Benzoic Acid Methylester
Reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[O:20][CH3:21])[CH:7]=[CH:6][C:5]=1[NH2:22].[H-].[Na+].[CH3:26]I>CN(C)C=O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[O:20][CH3:21])[CH:7]=[CH:6][C:5]=1[NH:22][CH3:26]Participants
5
Procedure
110 mg of 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-amino benzoic acid methylester are dissolved in 6 ml of dry dimethylformamide and treated with 13 mg of sodium hydride (80% in mineral oil). After stirring for 30 minutes at room temperature, 0.2 ml of methyl iodide are added and stirring continued overnight. The solvent is distilled off in vacuo, and the residue is partitioned between aqueous ph7 buffer solution and ethyl acetate. The separated organic layer is dried over magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel (hexane/ethyl acetate=7/1) to give the title compound as colourless crystals. mp: 73°.
Workup
- stirringstirring continued overnight
- distillationThe solvent is distilled off in vacuo
- customthe residue is partitioned between aqueous ph7 buffer solution and ethyl acetate
- dry with materialThe separated organic layer is dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue is chromatographed on silica gel (hexane/ethyl acetate=7/1)
Sources & evidence
- ORD record
- ord-2a2924bc14d84fe3a893cb5f4f7e4010
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05990116
Reaction notes
Loading…