(E)-Methyl 3-(2-amino-4-fluorophenyl)acrylate → 7-Fluoroquinolin-2(1H)-one
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([O:13]C)=O>C1COCC1.Cl>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:9]=[CH:10][C:11](=[O:13])[NH:1]2)=[CH:4][CH:5]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A mixture of (E)-methyl 3-(2-amino-4-fluorophenyl)acrylate (30.38 g, 156 mmol) in THF (400 mL) and 3M hydrochloric acid (400 mL) was heated at 65° C. for 20 h. The mixture was cooled to RT and poured onto ice. The resulting precipitate was filtered, washed with copious amounts of water and dried in vacuo to give 20.65 g (81%) of a light-yellow amorphous solid. m/z=164 (M+1).
Workup
- temperatureThe mixture was cooled to RT
- additionpoured onto ice
- filtrationThe resulting precipitate was filtered
- washwashed with copious amounts of water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-9ba7fd3c05aa4d91a64c2e198ff35b4b
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303028B2
Reaction notes
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