HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 559590Generated: October 31, 2026
8-Hydroxyquinoline → 1-(4-Amino-3-fluorophenyl)pyridin-2-one
https://huagongshe.com/reaction/559590
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 8-Hydroxyquinoline | HCID 1923 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Fluoro-4-iodoaniline | HCID 185694 | — |
| Reactant | HCID 178516071 | HCID 178516071 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | 1-(4-Amino-3-fluorophenyl)pyridin-2-one | HCID 22181548 | 89.8% |
Reaction Steps
A mixture of 2-fluoro-4-iodoaniline (3.00 g, 12.6 mmol), 2-hydroxypyridine 1-7 (1.20 g, 12.6 mmol), 8-hydroxyquinoline (0.184 g, 1.26 mmol) and K2CO3 (3.49 g, 25.3 mmol) in DMSO (20 mL) was degassed with Ar before being charged with CuI (0.241 g, 1.27 mmol). The mixture in a sealed tube was heated at 130° C. overnight. After being cooled down to room temperature, H2O and nBuOH were added. The organic phase was separated, concentrated in vacuo to give 1-(4-amino-3-fluorophenyl)pyridin-2(1H)-one as a solid (2.31 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08063077B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-ca5aef8f78084bebaa961d26b7f5f781 |
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| Source note | uspto-grants-2011_11 |
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