Sulfuric acid magnesium salt (1:1) → 1-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene-9-one

HRID 1027912Notes

Reaction equation

HRID 1027912 reaction equation
[C:1]1([NH:12][C:13](=[O:15])[CH3:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[O-:16]S([O-])(=O)=O.[Mg+2].[O-][Mn](=O)(=O)=O.[K+]>CC(C)=O>[O:16]=[C:7]1[C:6]2[C:1]([NH:12][C:13](=[O:15])[CH3:14])=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 102623081-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene

Product 1

HCID 103532981-Acetylamino-6,7,8,9-tetrahydro-5H-benzocycloheptene-9-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of the product from Example 132B (1 g, 4.92 mmol) in acetone (150 ml) was added 15% MgSO4 (15 mL). To the solution was added KMnO4 (1.944 g, 12.30 mmol) and stirred at ambient temperature for 2 hours. Then heated at slightly reflux for 40 hours. The mixture was filtered through diatomaceous earth, and washed with CH2Cl2. The organic was separated, diluted with CH2Cl2, washed with saturated Na2S2O3, dried and concentrated. The residue was purified by chromatography on silica gel column eluting with 20% EtOAc/hexanes to provide the title product. 1H NMR (DMSO-d6) δ 1.68-1.74 (m, 4H), 1.94 (s, 3H), 2.55-2.59 (m, 2H), 2.70 (t, J=6.04 Hz, 2H), 6.98 (d, J=7.34 Hz, 1H), 7.22 (d, J=7.34 Hz, 1H), 7.32 (t, J=7.70 Hz, 1H), 9.90 (s, 1H). MS (M+H)+ m/z 218.

Workup

  1. temperatureThen heated
  2. temperatureat slightly reflux for 40 hours
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. washwashed with CH2Cl2
  5. customThe organic was separated
  6. additiondiluted with CH2Cl2
  7. washwashed with saturated Na2S2O3
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica gel column
  11. washeluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-2bc92d0f0c5344e8a51e72a7ad869dc9
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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