Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 178522923 | HCID 178522923 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178493650 | HCID 178493650 | — |
Reaction Steps
N-((4-Chlorophenyl)methyl)-4-hydroxy-6,7,8-trifluoro-3-quinolinecarboxamide (366 mg) from Example No. 15 and sodium hydride (60% dispersion, 40 mg) are dissolved in DMF (10 mL) and to the mixture is added methanol (200 μL). Additional sodium hydride (40 mg) is added, and the mixture is heated at 140° C. for 1 h. The reaction mixture is allowed to cool to rt, poured into water (50 mL), acidified with acetic acid (10 mL), and is filtered. The crude product is purified by column chromatography (hexane/2-propanol, 95/5) to afford 68 mg of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06093732 |
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| Source dataset | uspto-grants-2000_07 |
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| ORD ID | ord-cea067265dcd492489737bffe25f5e11 |
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| Source note | uspto-grants-2000_07 |
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