Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Iodide Ion | HCID 30165 | — |
| Reactant | 6-Bromoquinoline | HCID 79243 | — |
| Catalyst | Copper | HCID 23978 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | 6-Iodoquinoline | HCID 20398553 | 80% |
Reaction Steps
6-bromoquinoline (80.1 g, 0.385 mol) is dissolved in n-butanol (0.8 L). Copper catalyst CuI (3.7 g, 0.019 mol), a copper-ligand N,N′-dimethylethylenediamine (3.4 g, 0.0385 mol) and an iodide source NaI (115.5 g, 0.770 mol) are added and the mixture is heated in a heating jacket, under inert atmosphere to 120° C. After work-up (0.8 L water is added to the reaction mixture, the organic layer is separated off and evaporated) and purification (the crude evaporation residue was crystallized from 150 mL diisopropylether), 6-iodoquinoline was obtained in 80% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08629144B2 |
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| Source dataset | uspto-grants-2014_01 |
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| ORD ID | ord-d0b1883730fe4c7eafa57729e9a888eb |
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| Source note | uspto-grants-2014_01 |
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