Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl Acrylate | HCID 7294 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | HCID 22052537 | HCID 22052537 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69652699 | HCID 69652699 | 50.4% |
Reaction Steps
A solution of 4.0 g (15.0 mmol) of 8-bromo-1,2,3,3a,5,9b-hexahydrocyclo-penta[c]quinolin-4-one (DE file number: 198 06 348.2) in 150 ml of DMF is heated for 4 hours to 120° C. with 2.7 ml (30.0 mmol) of acrylic acid-methyl ester, 4.2 ml (30 mmol) of triethylamine, 168 mg (0.75 mmol) of palladium(II) acetate and 457 mg (1.5 mmol) of tri-o-tolyl-phosphine. After 868 mg (0.75 mmol) of tetrakis(triphenylphosphine)palladium is added, the batch is stirred for 18 hours at 120° C., diluted at room temperature with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 2.05 g of product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07067667B2 |
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| Source dataset | uspto-grants-2006_06 |
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| ORD ID | ord-72bc5a2db8664ae186cde87ae56e9aa9 |
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| Source note | uspto-grants-2006_06 |
|---|