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

HRID 921967Notes

Reaction equation

HRID 921967 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-].[Cl-].[Cl-].[Al+3]>>[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-one

Conditions

Temperature
140 °C

Procedure

A mixture of 3-chloro-N-(2-fluorophenyl)propanamide (1-1, 17.2 g, 85.30 mmol) and aluminium trichloride (56.9 g, 427.0 mmol) was heated at 140° C. for 4 h under inert atmosphere. After cooling the reaction mixture down to 0° C., ice cold water (350 mL) was added slowly. The resulting precipitate was collected by filtration and washed with water and hexane. The crude compound was purified by flash chromatography on silica gel to obtain the title compound as a white solid. This intermediate was used directly in the next step without characterization.

Workup

  1. additionwas added slowly
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and hexane
  4. customThe crude compound was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-7d162daf2fe243e19f4af78062c54e49
Source dataset
uspto-grants-2016_03
Patent number
US09278093B2

Reaction notes

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