Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acrylate | HCID 8821 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 5-Bromo-3-methoxy-2-nitropyridine | HCID 817774 | — |
| Reactant | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66960160 | HCID 66960160 | 69% |
Reaction Steps
To a DMF (20 mL) solution of 5-bromo-3-methoxy-2-nitropyridine (726 mg) synthesized according to the method described in Acta Chemica Scandinavica vol. 47, p. 805, 1993, ethyl acrylate (0.44 mL), palladium acetate (35 mg), 2-(di-tert-butylphosphino) biphenyl (93 mg) and TEA (0.87 mL) were added, and the reaction solution was agitated at 80° C. for 3 hours. After the reaction solution was allowed to be cooled to room temperature, ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution to separate an organic layer. After the obtained organic layer was dried over anhydrous magnesium sulfate, solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 2:1), and 787 mg (69%) of (E)-3-(5-methoxy-6-nitropyridin-3-yl)acrylic acid ethyl ester was obtained. The physical properties of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07687640B2 |
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| Source dataset | uspto-grants-2010_03 |
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| ORD ID | ord-582af2d39f5a462cbe4c887d97658d2e |
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| Source note | uspto-grants-2010_03 |
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