Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 178496100 | HCID 178496100 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 58289508 | HCID 58289508 | — |
Reaction Steps
7-(2,2-Dimethoxy-ethoxy)-2-(4-isopropyl-thiazol-2-yl)-8-methyl-quinolin-4-ol (875 mg, 2.3 mmol) was dissolved in pyridine (20 mL). POCl3 (4.2 ml, 46.0 mmol) was added slowly. The reaction was heated at 80° C. for 4 hours. The reaction was cooled to 0° C. and methanol (5 mL) was added. The reaction was neutralized with a saturated aqueous sodium bicarbonate solution. The product was extracted with ethyl acetate (3×20 mL). The combined organics were dried with sodium sulfate, filtered and was concentrated. 4-Chloro-7-(2,2-dimethoxy-ethoxy)-2-(4-isopropyl-thiazol-2-yl)-8-methyl-quinoline (410 mg, 44%) was purified by silica gel chromatography.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08927484B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-2afc8eddc93d4930a71724e0cf0d44c9 |
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| Source note | uspto-grants-2015_01 |
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