Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Butylamine | HCID 8007 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline | HCID 11301470 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 22667087 | HCID 22667087 | 178.7% |
Reaction Steps
4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (100 mg) was dissolved in toluene (8 ml) and triethylamine (1.0 ml) with heating, and a solution of triphosgene (47 mg) in toluene (1.0 ml) was then added to the solution. The mixture was heated under reflux for 5 min. Next, butylamine (80 mg) was added to the reaction solution, and the mixture was heated under reflux for additional 5 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/acetone (2/1) to give 117 mg (yield 81%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07169789B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-c4e4b095893141b6b6f5333c2d588208 |
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| Source note | uspto-grants-2007_01 |
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