Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-chloro-1,8-naphthyridin-2(1H)-one | HCID 10607482 | — |
| Reactant | 7-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid | HCID 14541268 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58902304 | HCID 58902304 | 71% |
Reaction Steps
A suspension of 5-chloro-1,8-naphthyridin-2(1H)-one (0.050 g, 0.00028 mol), 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (0.080 g, 0.00042 mol), and cesium carbonate (0.270 g, 0.000829 mol) in DMF (1 mL) was subjected to microwave heating (180° C.) for 15 min. The reaction mixture was dissolved in water and then acidified to pH of 2 with 1N HCl. The mixture was extracted with EtOAc (4×). The combined organic solutions were dried over MgSO4, filtered, and concentrated. The residue was triturated with DCM and hexanes to produce 7-[(7-oxo-7,8-dihydro-1,8-naphthyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid as a white solid (0.066 g, 71%). LCMS: (FA) ES+ 337.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08110687B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-75e6d1fa399b4847aaeed460ceea5c9f |
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| Source note | uspto-grants-2012_02 |
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