HCID 86649425, compound → 7-Fluoro-6-(trifluoromethyl)-2(1H)-quinolinone
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1/[CH:13]=[CH:14]/[C:15]([O:17]CC)=O>Cl.O1CCOCC1>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:13]=[CH:14][C:15](=[O:17])[NH:1]2)=[CH:4][C:5]=1[C:9]([F:12])([F:11])[F:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a stirring mixture of (E)-ethyl 3-(2-amino-4-fluoro-5-(trifluoromethyl)phenyl)acrylate in 4N HCl in dioxane (10 mL) was added concentrated HCl (2 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)=1.887, method [1], MS (ESI) 232.0 (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-8a82077600eb4b85849b28e421274027
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450363B2
Reaction notes
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