Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 3-chloro-3-oxopropionate | HCID 118931 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Reactant | 1-(2-Amino-4-(trifluoromethyl)phenyl)ethan-1-one | HCID 46835500 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178470056 | HCID 178470056 | 87.5% |
Reaction Steps
12.6 ml (0.09 mol) NEt3 was added to a solution of 16.6 g (0.08 mol) 1-(2-amino-4-(trifluoromethyl)phenyl)ethanone in DCM (170 ml) and cooled to 0° C. 13.4 ml (0.11 mol) 3-chloro-3-oxo-propanoic acid ethyl ester was subsequently added in drops and the mixture was then stirred for 16 h at RT. The mixture was then diluted with water and extracted with DCM (3×). The combined organic phases were dried over Na2SO4 and concentrated in a vacuum. After CC (EtOAc/hexane 2:3) of the residue, 18.1 g (0.07 mol, 87%) 2-hydroxy-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08445512B2 |
|---|
| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-8cb1cb5414104e9d8db05bfdb4ed0de6 |
|---|
| Source note | uspto-grants-2013_05 |
|---|
