Acetone → N-(8-Oxo-5,6,7,8-tetrahydronaphthalen-1-YL)acetamide

HRID 964638Notes

Reaction equation

HRID 964638 reaction equation
[C:1]([NH:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].CC(C)=[O:17].S([O-])([O-])(=O)=O.[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+]>C(Cl)(Cl)Cl.O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 11063199N-(1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Product 1

HCID 12119265N-(8-Oxo-5,6,7,8-tetrahydronaphthalen-1-YL)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

10 gm of 1-acetylamino-tetraline was dissolved into a mixed solvent of 400 ml acetone and 40 ml of 15% aqueous solution of magnesium sulfate. The solution was kept at 0° C. to add 42 gm of potassium permanganate, followed by stirring for 20 minutes at the same temperature. 800 ml of water was added to the residue obtained by concentrating the solvent. Precipitates thus obtained was extracted with chloroform and the extract was washed with brine and dried over magnesium sulfate. The residue obtained by the concentration of the solvent was subjected to silica gel column chromatography using chloroform as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 5.46 gm of the title compound.

Workup

  1. customwas kept at 0° C.
  2. customobtained
  3. concentrationby concentrating the solvent
  4. customPrecipitates thus
  5. customobtained
  6. extractionwas extracted with chloroform
  7. washthe extract was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe residue obtained by the concentration of the solvent
  10. customto obtain fractions
  11. additioncontaining the target compound
  12. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-6315f1f1a9fb4ed19521e6ba2b029f8d
Source dataset
uspto-grants-1998_06
Patent number
US05770605

Reaction notes

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