Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formamide | HCID 713 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 18426713 | HCID 18426713 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18426727 | HCID 18426727 | 89.6% |
Reaction Steps
A mixture of 1-butyl-3-ethoxycarbonyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine (45.0 g, 120 mmol), formamide (15.5 ml, 390 mmol) and dimethylformamide (120 ml) was dissolved at 60° C., and thereto was added a 25% solution of sodium methoxide in methanol (108 ml, 390 mmol), and the mixture was stirred at 60° C. for 9 hours. The mixture was cooled to 0° C., and thereto was added water (1.2 liter), and the mixture was stirred for 15 minutes. The precipitated solid was collected by filtration, washed with ethanol, and dried to give the title compound (37.8 g, yield; 87%) as white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06300500B1 |
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| Source dataset | uspto-grants-2001_10 |
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| ORD ID | ord-5b43af2fdffc42c98919258c5d7d2291 |
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| Source note | uspto-grants-2001_10 |
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