Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Bromoethyl methyl ether | HCID 80972 | — |
| Reactant | 2-chloroquinolin-5-ol | HCID 135442221 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | HCID 86634195 | HCID 86634195 | 32.4% |
Reaction Steps
2-Chloro-quinolin-5-ol (CAS 124467-35-2) (0.3 g, 1.56 mmol) was dissolved in acetone (10 mL) and potassium carbonate (0.368 g, 2.75 mmol) was added. After addition of 2-bromethylmethylether (0.25 ml, 2.7 mmol) the reaction mixture was stirred for 18 h at 50° C. Then water was added and the mixture was extracted with ethyl acetate (3×). The combined organic phases were dried, filtered and concentrated. The residue was subjected to column chromatography (silica gel, heptane/ethyl acetate 9:1/4:1) to yield 2-chloro-5-(2-methoxy-ethoxy)-quinoline as a colourless oil (0.12 g, 30%). MS: m/e=238.8 (M+H+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07989628B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-52db8e71b7d94c03953ac3b56d387714 |
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| Source note | uspto-grants-2011_08 |
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