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

HRID 2364572Notes

Reaction equation

HRID 2364572 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-0887b670843f4f5d8f9f7a32f1694c72
Source dataset
uspto-grants-2014_04
Patent number
US08691986B2

Reaction notes

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