Water → HCID 18317731, compound

HRID 1700701Notes

Reaction equation

HRID 1700701 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:21]C)=[C:7]([CH:9]2[CH2:18][C:17]3[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=3[C:11](=[O:20])[CH2:10]2)[CH:8]=1.O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[F:2][C:3]1[CH:4]=[CH:5][C:6]([OH:21])=[C:7]([CH:9]2[CH2:18][C:17]3[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=3[C:11](=[O:20])[CH2:10]2)[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 18317355HCID 18317355, compound

Product 1

HCID 18317731HCID 18317731, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 7-(5-fluoro-2-methoxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one hydrochloride (2.13 g) were added water (20 ml), anhydrous potassium carbonate (1.5 g) and ethyl acetate (50 ml). The mixture was shaken, and the separated upper layer was concentrated under reduced pressure. The residue was dissolved in dichloromethane (15 ml), and to the solution was added dropwise a solution of 1M-boron tribromide-dichloromethane (21 ml), while stirring in ice-cooling bath. The bath was removed, and the mixture was stirred for 2 hours, and poured onto ice-water. To the mixture was added excess amount of sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified with silica gel column chromatography to give 7-(5-fluoro-2-hydroxyphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.773 g).

Workup

  1. concentrationthe separated upper layer was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (15 ml)
  3. additionto the solution was added dropwise a solution of 1M-boron tribromide-dichloromethane (21 ml)
  4. stirringwhile stirring in ice-
  5. temperaturecooling bath
  6. customThe bath was removed
  7. stirringthe mixture was stirred for 2 hours
  8. additionpoured onto ice-water
  9. additionTo the mixture was added excess amount of sodium hydrogen carbonate solution
  10. extractionthe mixture was extracted with ethyl acetate
  11. concentrationThe extract was concentrated under reduced pressure
  12. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-9e5cbf1b84ca4c5b96b2963bfb9d7afc
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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