HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 6,7-Dimethoxy-4-[(1-methyl-5-indolyl)oxy]quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinoline | HCID 22132645 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6,7-Dimethoxy-4-[(1-methyl-5-indolyl)oxy]quinoline | HCID 23156648 | 62% |
Reaction Steps
6,7-Dimethoxy-4-[(1H-5-indolyl)oxy]quinoline (50 mg) was dissolved in N,N-dimethylformamide (1 ml), and 60% sodium hydride (7 mg) was added, followed by stirring for 30 min under ice cooling. Methyl iodide (0.0107 ml) was added to the reaction solution, and the mixture was stirred under ice cooling for additional one hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using methanol-chloroform to give the title compound (32 mg, yield 62%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07560558B2 |
| Source dataset | uspto-grants-2009_07 |
| ORD ID | ord-9122da5cd3ec4bf0beaa10e363c6457e |
| Source note | uspto-grants-2009_07 |