3-chloro-N-(3-fluorophenyl)propanamide → Carbostyril, 3,4-dihydro-7-fluoro-

HRID 1520182Notes

Reaction equation

HRID 1520182 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-]>>[F:13][C:9]1[CH:8]=[C:7]2[C:12]([CH2:2][CH2:3][C:4](=[O:5])[NH:6]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 35556953-chloro-N-(3-fluorophenyl)propanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 138300Carbostyril, 3,4-dihydro-7-fluoro-Yield 61%

Conditions

Temperature
120 °C

Procedure

To the solid of 3-chloro-N-(3-fluorophenyl)propanamide (3 g, 14.88 mmol) was added AlCl3 (6.3 g, 0.047 mmol) and maintained with an inert atmosphere of nitrogen with stirring for 5 h at 120° C. The reaction was then quenched with ice-water, extracted with ethyl acetate (3×50 ml) and the organic layers were combined, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography with 4% ethyl acetate in petroleum ether to afford 7-fluoro-1,2,3,4-tetrahydroquinolin-2-one as a white solid (1.5 g, 61%).

Workup

  1. temperaturemaintained with an inert atmosphere of nitrogen
  2. customThe reaction was then quenched with ice-water
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography with 4% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-b2f0b8c4ec974f4b95a3a902cc1ebdb3
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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