Methane → HCID 58119731, compound

HRID 2368635Notes

Reaction equation

HRID 2368635 reaction equation
[CH:1]1([CH:6]2[C:15]3[C:14](=[O:16])[CH2:13][C:12]([CH3:18])([CH3:17])[CH2:11][C:10]=3[NH:9][C:8]([CH:19]([O:21][CH3:22])[CH3:20])=[C:7]2[C:23](=[O:34])[C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C>ClCCl.C1CCCCC1.C(OC(=O)C)C>[CH:1]1([C:6]2[C:15]3[C:14](=[O:16])[CH2:13][C:12]([CH3:17])([CH3:18])[CH2:11][C:10]=3[N:9]=[C:8]([CH:19]([O:21][CH3:22])[CH3:20])[C:7]=2[C:23](=[O:34])[C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 297MethaneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 58119790HCID 58119790, compound

Product 1

HCID 58119731HCID 58119731, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

4.7 g 4-Cyclopentyl-2-(1-methoxy-ethyl)-7,7-dimethyl-3-(4-trifluoromethyl-benzoyl)-4,6,7,8-tetrahydro-1H-quinolin-5-one are dissolved in 100 ml dichloromethane, cooled to 0° C. and 2.5 g 2,3-dichloro-5,6-dicyano-p-benzoquinone are added portionwise. The temperature is raised during 3 hours to room temperature. Then the volume is reduced to approximately 60 ml by evaporation in vacuo, the mixture is filtered and the filter cake is washed 5 times with 50 ml of dichloromethane. The combined organic phases are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 90:10 to 50:50). The product thus obtained is dissolved in cyclohexane/ethylacetate 70:30 and treated with charcoal. The mixture is filtered and the charcoal is washed 3 times with 100 ml cyclohexane/ethylacetate 70:30. The combined organic phases are evaporated in vacuo.

Workup

  1. temperatureThe temperature is raised during 3 hours to room temperature
  2. customThen the volume is reduced to approximately 60 ml by evaporation in vacuo
  3. filtrationthe mixture is filtered
  4. washthe filter cake is washed 5 times with 50 ml of dichloromethane
  5. customThe combined organic phases are evaporated in vacuo
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 90:10 to 50:50)
  7. customThe product thus obtained
  8. filtrationThe mixture is filtered
  9. washthe charcoal is washed 3 times with 100 ml cyclohexane/ethylacetate 70:30
  10. customThe combined organic phases are evaporated in vacuo

Sources & evidence

ORD record
ord-33b8e0f9f46843cd832816c61e0e7682
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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