Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Aminophenol | HCID 5801 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one | HCID 58168008 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58168040 | HCID 58168040 | 12.7% |
Reaction Steps
1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 2-aminophenol (43 mg, 0.39 mmol), and potassium carbonate (90 mg, 0.65 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, and filtered through a membrane. The crude product was purified via prep-LC-MS to provide 133 (5 mg, 12% yield) as a solid. LC-MS (M+H=304, obsd.=304). 1H NMR (400 MHz, d6-DMSO): δ 11.72 (s, 1H), 9.68 (s, 2H), 8.88 (d, 1H), 8.35 (d, 1H), 8.18 (m, 1H), 8.01 (d, 1H), 7.76 (t, 1H), 7.58 (t, 1H), 7.02 (m, 2H), 6.78 (t, 1H), 6.48 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08735584B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-4c8bf03fc64245dcad10d27cd75672e9 |
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| Source note | uspto-grants-2014_05 |
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