2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 71679545, compound

HRID 881994Notes

Reaction equation

HRID 881994 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([CH2:15][CH:16]([C:21]([CH2:23][Si](C)(C)C)=[CH2:22])[CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:7][CH2:6]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:17]([CH:16]1[CH2:15][N:8]2[CH2:7][CH2:6][C:5]3[C:10]([CH:9]2[CH2:22][C:21]1=[CH2:23])=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:18]([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 56933724HCID 56933724, compound2×

Product 1

HCID 71679545HCID 71679545, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6,7-dimethoxy-2-(4-methyl-2(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl)-1,2,3,4-tetrahydroisoquinoline (Formula 5; 18.4 mg, 0.0693 mmol) and a 4 Å molecular sieve (100 mg) were put into anhydrous CH2Cl2 (0.5 mL) and stirred. A solution obtained by dissolving 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ; 19.3 mg, 0.104 mmol) and LiClO4 (2.19 mg, 0.0208 mmol) in anhydrous CH2Cl2 (0.5 mL) in a separate container was slowly added to the reaction solution and stirred for 20 min. A saturated NaHCO3 aqueous solution (1 mL) was added thereto to complete the reaction. An organic layer was extracted, and then the organic layer collected was washed with distilled water and a brine solution. Anhydrous magnesium sulfate was used to dry the organic layer, filtration under reduced pressure and evaporation under reduced pressure were performed, and then column chromatography was used to obtain 8.22 mg (yield 55%) of the title compound.

Workup

  1. customA solution obtained
  2. additionwas slowly added to the reaction solution
  3. stirringstirred for 20 min
  4. customthe reaction
  5. extractionAn organic layer was extracted
  6. customthe organic layer collected
  7. washwas washed with distilled water
  8. customto dry
  9. filtrationthe organic layer, filtration
  10. customunder reduced pressure and evaporation under reduced pressure

Sources & evidence

ORD record
ord-b9cdf2101f5940ce8eefb810a75e46b6
Source dataset
uspto-grants-2015_03
Patent number
US08993766B2

Reaction notes

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