N-(3-Fluoro-4-methyl-5-oxo-5,6,7,8-tetrahydro-1-naphthyl)acetamide → N-(3-Fluoro-4-methyl-5,6,7,8-tetrahydro-1-naphthyl)acetamide
Reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[C:13]([F:15])[C:12]([CH3:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=O)(=[O:3])[CH3:2].[H][H]>[C].[Pd].CO>[C:1]([NH:4][C:5]1[CH:14]=[C:13]([F:15])[C:12]([CH3:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10]2)(=[O:3])[CH3:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
In a 50-ml autoclave, 1.0 g of 5-acetylamino-7 -fluoro-8-methyl-l-tetralone and 10 ml of methanol were charged. To the resulting mixture, 0.5 g of 10% palladium-carbon was added. The hydrogen pressure was increased to 40 kg/cm2 at room temperature, under which the resulting mixture was stirred at 50° C. for 18 hours. After the completion of the reaction, the reaction mixture was filtered. The catalyst so obtained was washed with chloroform and then the filtrate was concentrated under reduced pressure. To the residue, isopropyl ether was added. The crystals so precipitated were collected by filtration, followed by drying under reduced pressure, whereby 0.76 g of the title compound was obtained.
Workup
- customAfter the completion of the reaction
- filtrationthe reaction mixture was filtered
- customThe catalyst so obtained
- washwas washed with chloroform
- concentrationthe filtrate was concentrated under reduced pressure
- additionTo the residue, isopropyl ether was added
- customThe crystals so precipitated
- filtrationwere collected by filtration
- customby drying under reduced pressure
Sources & evidence
- ORD record
- ord-25d2f2f9781a4804bd7db89a0ea1fa19
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849945
Reaction notes
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