Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Butyl bromide | HCID 8002 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Reactant | HCID 86662686 | HCID 86662686 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66584541 | HCID 66584541 | 40% |
Reaction Steps
A solution of 1.0 g (3.3 mmol) 4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylate (for synthesis see example 1, section a)) in DMSO (9 ml) was treated with 461 mg (3.3 mmol) K2CO3 and 360 μl (3.3 mmol) 1-bromobutane at RT and was subsequently heated at 50° C. for 90 mins. After cooling to RT the RS was diluted with water (30 ml) and extracted with EtOAc (3×50 ml). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo. After CC (EtOAc/hexane 1:8) of the residue, 480 mg (1.4 mmol, 40%) ethyl 1-butyl-4-methyl-2-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylate was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08653102B2 |
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| Source dataset | uspto-grants-2014_02 |
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| ORD ID | ord-59e014517e674f88a39fef60a0e996fd |
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| Source note | uspto-grants-2014_02 |
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