Hydrochloric Acid → N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

HRID 1458312Notes

Reaction equation

HRID 1458312 reaction equation
[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([NH:17]C(=O)C)[CH:9]=[C:10]([F:16])[C:11]=2[CH3:15])[C:6]1=[O:21])(=[O:3])[CH3:2].Cl.C(=O)([O-])[O-].[K+].[K+].[O-][Si]([O-])=O.[Mg+2]>O>[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([NH2:17])[CH:9]=[C:10]([F:16])[C:11]=2[CH3:15])[C:6]1=[O:21])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 61680MAGNESIUM SILICATE (synthetic)HCID 22080992N,N'-(3-Fluoro-4-methyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,7-diyl)diacetamide

Product 1

HCID 10220585N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamideYield 49.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 8.0 g of 2,8-diacetylamino-6-fluoro-5-methyl-1 -tetralone, 120 ml of a 20% aqueous solution of hydrochloric acid were added and the mixture was stirred at an external temperature of 60° C. for 2 hours. After the completion of the reaction, the reaction mixture was cooled and was added with 100 ml of water. The resulting mixture was filtered through a Kiriyama funnel. To the filtrate, further 100 ml of water were added, followed by extraction with chloroform. To the chloroform layer so obtained, potassium carbonate and Florisil were added and they were stirred for a while. The resulting mixture was filtered and then, the solvent was removed under reduced pressure. The residue so obtained was recrystallized from chloroform-diethyl ether, whereby 3.4 g of the title compound was obtained.

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe reaction mixture was cooled
  3. filtrationThe resulting mixture was filtered through a Kiriyama funnel
  4. additionTo the filtrate, further 100 ml of water were added
  5. extractionfollowed by extraction with chloroform
  6. customTo the chloroform layer so obtained
  7. stirringthey were stirred for a while
  8. filtrationThe resulting mixture was filtered
  9. customthe solvent was removed under reduced pressure
  10. customThe residue so obtained
  11. customwas recrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-98049c7fd27445eb97fca3f5795de2e8
Source dataset
uspto-grants-1998_12
Patent number
US05849945

Reaction notes

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