HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1987172Generated: October 31, 2026
8-Hydroxyquinoline → 1-(4-Amino-3-fluorophenyl)pyridin-2-one
https://huagongshe.com/reaction/1987172
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 8-Hydroxyquinoline | HCID 1923 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Bromo-2-fluoroaniline | HCID 123050 | — |
| Reactant | HCID 178516071 | HCID 178516071 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 1-(4-Amino-3-fluorophenyl)pyridin-2-one | HCID 22181548 | — |
Reaction Steps
4-Bromo-2-fluoroaniline (13.0 g; 68 mmol), 2-hydroxypyridine (9.11 g; 96 mmol), 8-hydroxyquinoline (1.5 g; 10 mmol) are dissolved under argon in DMSO (40 ml). To this solution K2CO3 (10.4 g; 75 mmol) and CuI (1.95 g; 10 mmol) are added and the resulting suspension is heavily stirred under argon at 150° C. for 18 h. The mixture is evaporated to dryness under reduced pressure and the final residue is chromatographed over silica gel (400 g) using dichloromethane/methanol as eluents. The obtained crude product is recrystallized with diethyl ether to yield an off-white solid. Yield: 2.80 g (20.0%), ESI-MS: m/z=205 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07550487B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-c92fb226905a483c97c4efa45689d654 |
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| Source note | uspto-grants-2009_06 |
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