(E)-Methyl 3-(2-amino-4-fluorophenyl)acrylate → 7-Fluoroquinolin-2(1H)-one

HRID 624516Notes

Reaction equation

HRID 624516 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]=1

Participants

4

Reactant 1

HCID 23003313(E)-Methyl 3-(2-amino-4-fluorophenyl)acrylate

Product 1

HCID 190675757-Fluoroquinolin-2(1H)-oneYield 81.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

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

  1. temperatureThe mixture was cooled to RT
  2. additionpoured onto ice
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with copious amounts of water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9ba7fd3c05aa4d91a64c2e198ff35b4b
Source dataset
uspto-grants-2016_04
Patent number
US09303028B2

Reaction notes

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