Hydrochloric Acid → N-(3-Fluoro-4-methyl-5-oxo-5,6,7,8-tetrahydro-1-naphthyl)acetamide

HRID 1458309Notes

Reaction equation

HRID 1458309 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([CH3:12])=[CH:7][C:6]=1[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)(=[O:3])[CH3:2].S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].Cl.C(OC(C)C)(C)C>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([CH3:12])=[C:7]2[C:6]=1[CH2:13][CH2:14][CH2:15][C:16]2=[O:18])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 224449504-(2-Acetamido-4-fluoro-5-methylphenyl)butanoic acid

Product 1

HCID 22101954N-(3-Fluoro-4-methyl-5-oxo-5,6,7,8-tetrahydro-1-naphthyl)acetamideYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of methylene chloride, 5.0 g of 4-(2 -acetylamino-4-fluoro-5-methylphenyl)butanoic acid was suspended. To the suspension, 4.3 ml of thionyl chloride was added dropwise over 2 minutes at an internal temperature of 3° to 4° C., followed by stirring at the same temperature for 15 minutes and then at room temperature for 45 minutes. To the resulting mixture, 6.6 g of aluminum chloride were added over 5 minutes at an internal temperature of 4° to 6° C., followed by stirring for one hour at the same temperature and then stirring for 24 hours at room temperature. After the completion of the reaction, a 5% aqueous hydrochloric acid solution and ice were added gradually to the reaction mixture and they were stirred for a while. The reaction mixture was extracted with chloroform. The chloroform layer was washed sufficiently with water and a saturated aqueous solution of sodium bicarbonate, and was then dried over potassium carbonate. The solvent was removed under reduced pressure. To the residue so obtained, isopropyl ether was added. The crystals so precipitated were collected by filtration, whereby 3.5 g of the title compound was obtained.

Workup

  1. waitat room temperature for 45 minutes
  2. stirringby stirring for one hour at the same temperature
  3. stirringstirring for 24 hours at room temperature
  4. customAfter the completion of the reaction
  5. stirringwere stirred for a while
  6. extractionThe reaction mixture was extracted with chloroform
  7. washThe chloroform layer was washed sufficiently with water
  8. dry with materiala saturated aqueous solution of sodium bicarbonate, and was then dried over potassium carbonate
  9. customThe solvent was removed under reduced pressure
  10. customTo the residue so obtained
  11. customThe crystals so precipitated
  12. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3f9db8c4cca04839b8b1e229ee5eac3d
Source dataset
uspto-grants-1998_12
Patent number
US05849945

Reaction notes

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