Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Methyl 3-mercaptopropionate | HCID 18050 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 2-Chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester | HCID 86645340 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68507420 | HCID 68507420 | 50% |
Reaction Steps
336 mg (3.0 mmol) potassium tert-butylate were added to a solution of 360 mg (3.0 mmol) 3-mercaptopropionic acid methyl ester in DMF (8 ml) at 0° C. and the mixture was stirred for 30 min at 0° C. Then 953 mg (3.0 mmol) 2-chloro-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester were added and the reaction solution was heated slowly to 50° C. and stirred for 16 h at this temperature. After cooling to RT the mixture was diluted with water and extracted with EE. The organic phase was dried over MgSO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 9:1) of the residue yielded 625 mg (1.5 mmol, 50%) 2-(3-ethoxy-3-oxopropylthio)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399673B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-8dd2f91ceceb464dad5c6f9a54f98b7b |
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| Source note | uspto-grants-2013_03 |
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