Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ethyl 7,8-difluoro-1,4-dihydro-1-oxobenzo[f][1,7]naphthyridine-2-carboxylate | HCID 18523347 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 18523248 | HCID 18523248 | 69.6% |
Reaction Steps
A suspension of 35 g of ethyl 7,8-difluoro-1-oxo-1,4-dihydrobenzo[f][1,7]-naphthyridine-2-carboxylate and 31.8 g of potassium carbonate in 350 cm3 of dimethyl sulphoxide was heated, with stirring, at a temperature of 90° C. for 3 hours. After cooling to 50° C., 65 g of methyl iodide were added; the mixture was heated at 90° C. for 3 hours. After cooling to 20° C., the insoluble material was dewatered, washed 4 times with 100 cm3 of water, 3 times with 100 cm3 of ethanol, and twice with 100 cm3 of diethyl ether. 25.5 g of ethyl 7,8-difluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate was obtained in the form of white crystals, which melted at 320° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06566362B2 |
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| Source dataset | uspto-grants-2003_05 |
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| ORD ID | ord-179f98dba06644a0b17f8182fdb7f904 |
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| Source note | uspto-grants-2003_05 |
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