Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 57671722 | HCID 57671722 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 57671962 | HCID 57671962 | 47% |
Reaction Steps
A mixture of 8-(5-fluoro-2-methylphenoxymethyl)-7-(2-methoxy-5-nitrophenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 6-27, 18.8 mg, 0.0392 mmol) and tin chloride (II) (23.0 mg, 0.121 mmol) was suspended in mixed solvent of anhydrous N,N-dimethylformamide (0.25 ml) and anhydrous ethanol (0.5 mL), and stirred at 80° C. overnight. After cooling down, the reaction mixture was diluted with ethyl acetate (10 mL) and saturated aqueous sodium hydrogen carbonate solution was added thereto until the pH became 9. After the precipitate was filtered, the filtrate was washed with water (50 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (8.2 mg) as a brown solid. (Yield 47%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08975256B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-b086199e6e204f72a83a0ee47e418014 |
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| Source note | uspto-grants-2015_03 |
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