(E)-Ethyl 3-(2-amino-5-(trifluoromethyl)phenyl)acrylate → 6-(Trifluoromethyl)quinolin-2(1H)-one
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1/[CH:12]=[CH:13]/[C:14]([O:16]CC)=O>Cl.O1CCOCC1>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:14](=[O:16])[CH:13]=[CH:12]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a stirring mixture of (E)-ethyl 3-(2-amino-5-(trifluoromethyl)phenyl)acrylate (4 g, 15.4 mmol) in 4N HCl in dioxane (20 mL) was added concentrated HCl (3 mL). The resulting mixture was warmed to 100° C. overnight. The reaction mixture was cooled to rt and then slowly quenched with a cold saturated NaHCO3 solution until pH>7. A normal aqueous extraction with EtOAc was followed. The crude mixture was taken directly to the next reaction without further purification. Retention time(min)=1.849, method [1], MS(ESI) 214.0 (M+H).
Workup
- temperatureThe reaction mixture was cooled to rt
- customslowly quenched with a cold saturated NaHCO3 solution until pH>7
- extractionA normal aqueous extraction with EtOAc
- customThe crude mixture was taken directly to the next reaction without further purification
Sources & evidence
- ORD record
- ord-63b79ea66fc4422d85561a9f228417f6
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073891B2
Reaction notes
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