Sodium Hydroxide → HCID 13960198, compound

HRID 2413956Notes

Reaction equation

HRID 2413956 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[F:15])[NH:5][CH:6]([CH3:11])[CH2:7][C:8]([OH:10])=O.[OH-].[Na+]>O>[Cl:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[C:4]2[C:3]=1[C:8](=[O:10])[CH2:7][CH:6]([CH3:11])[NH:5]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14076517HCID 14076517, compound

Product 1

HCID 13960198HCID 13960198, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

400 g of polyphosphoric acid was added to 92.66 g (0.40 mole) of the 3-(3-chloro-4-fluoroanilino) butyric acid and this mixture was stirred at 110° C. for 1.5 hours. After being allowed to cool to room temperature, the resulting reaction solution was diluted with 3 liters of water and then adjusted to pH 4-5 with an aqueous sodium hydroxide solution. Then, the solid matter which separated out was extracted with chloroform and this extract was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (using chloroform as the developing solvent). The fraction containing the desired product was evaporated to dryness under reduced pressure and the resulting residue was recrystallized from benzene to obtain 7.43 g (8.7% yield) of 5-chloro-6-fluoro-2-methyl-4-oxo-1,2,3, 4-tetrahydroquinoline in the form of yellow crystals. On the other hand, another fraction was worked up in the same manner as above to obtain 8.55 g (10.0% yield) of a structural isomer thereof, or 7-chloro-6-fluoro-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline, in the form of yellow crystals.

Workup

  1. temperatureto cool to room temperature
  2. customthe resulting reaction solution
  3. customThen, the solid matter which separated out
  4. extractionwas extracted with chloroform
  5. concentrationthis extract was concentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (
  8. additionThe fraction containing the desired product
  9. customwas evaporated to dryness under reduced pressure
  10. customthe resulting residue was recrystallized from benzene

Sources & evidence

ORD record
ord-0f48c98698fb4883953466febd1cbd2c
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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