Sodium Hydroxide → HCID 13960198, compound

HRID 1708885Notes

Reaction equation

HRID 1708885 reaction equation
Br[C:2]1[CH:14]=[C:13]([F:15])[C:12]([Cl:16])=[CH:11][C:3]=1[NH:4][CH:5]([CH3:10])[CH2:6][C:7]([OH:9])=O.P(OCC)(OCC)(OCC)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+].[H][H]>[Pd].CO.O>[Cl:16][C:12]1[C:13]([F:15])=[CH:14][CH:2]=[C:3]2[C:11]=1[C:7](=[O:9])[CH2:6][CH:5]([CH3:10])[NH:4]2

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 14881053HCID 14881053, compoundHCID 131716493HCID 131716493, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13960198HCID 13960198, compoundYield 53.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6.0 g of (+)-3-(2-bromo-5-chloro-4fluoroanilino)butyric acid obtained in Example 5 was added to 60 g of a triethyl phosphate-phosphorus pentoxide mixture (in a weight ratio of 3:2). The resulting mixture was stirred at 80°-90° C. for 15 minutes and then cooled to room temperature. After the addition of 600 ml of water, the resulting mixture was stirred and then extracted twice with 150 ml-portions of chloroform. The extract was washed twice with 200 ml-portions of water, dried and then concentrated under reduced pressure. The residue thus obtained was mixed with 0.1 g of 10% palladium-active carbon, 20 ml of a 1N aqueous solution of sodium hydroxide, and 200 ml of methanol. The resulting mixture was stirred at ordinary temperature and pressure for an hour with hydrogen gas passed therethrough. This reaction mixture was filtered to remove the palladium-active carbon therefrom, the filtrate was concentrated under reduced pressure, and the resulting residue was extracted with chloroform. The extract was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography [using n-hexane-ethyl acetate (5:1) as the eluent]. Fractions containing the desired compound were collected and concentrated under reduced pressure to obtain 2.2 g of (-)-5-chloro 6-fluoro-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline.

Workup

  1. stirringthe resulting mixture was stirred
  2. extractionextracted twice with 150 ml-portions of chloroform
  3. washThe extract was washed twice with 200 ml-portions of water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. filtrationThis reaction mixture was filtered
  8. customto remove the palladium-active carbon
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. extractionthe resulting residue was extracted with chloroform
  11. concentrationThe extract was concentrated under reduced pressure
  12. customthe resulting residue was purified by silica gel column chromatography [
  13. additionFractions containing the desired compound
  14. customwere collected
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97bdcd1f712749d0b06ead284d3108d4
Source dataset
uspto-grants-1990_08
Patent number
US04946844

Reaction notes

Loading…