3-chloro-N-(2-fluorophenyl)propanamide → 8-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

HRID 1774837Notes

Reaction equation

HRID 1774837 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=[O:5].[Cl-].[Al+3].[Cl-].[Cl-]>>[F:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

Participants

3

Reactant 2

HCID 42560293-chloro-N-(2-fluorophenyl)propanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-oneYield 70.8%

Conditions

Temperature
160 °C

Procedure

A flame-dried 50-mL flask equipped with a magnetic stirring bar was charged with 3-chloro-N-(2-fluoro-phenyl)-propionamide (5.33 g, 26.5 mmol) and aluminium chloride (5.30 g, 39.7 mmol). In a pre-heated oil bath, the flask was heated at 160° C. for 1.5 hours. After cooling to room temperature, the mixture was treated slowly with ice-water and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford title compound (3.1 g, 70%) as a solid. MS: 166.0 (M+H+)+.

Workup

  1. customA flame-dried 50-mL flask equipped with a magnetic stirring bar
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine in sequence
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a9e56bb2038648dea36f70c9202f2d04
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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