2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 66881314, compound

HRID 1893568Notes

Reaction equation

HRID 1893568 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].ClC1[C:16](=[O:27])[C:17](C#N)=[C:18](C#N)[C:19](=O)[C:20]=1Cl.O1C=CCCC1>C(#N)C>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][O:27]2)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 80803,4-dihydro-2H-pyranHCID 14800346-methyl-5-nitro-1H-indazole

Product 1

HCID 66881314HCID 66881314, compoundYield 716.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Methyl-5-nitro-1H-indazole (15.1 g, 85.2 mmol), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (1.94 g, 8.55 mmol) and 3,4-dihydro-2H-pyran (9.0 ml, 98.4 mmol) were dissolved in acetonitrile (300 ml), and the mixture was heated under reflux for 4.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with an ethyl acetate-hexane=1:1 mixed solvent, washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (16.0 g, yield 72%) as an orange solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4.5 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with an ethyl acetate-hexane=1:1 mixed solvent
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure
  9. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-37a56e657f8d4bd5957f54d7f79e607b
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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