2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19036494, compound

HRID 264459Notes

Reaction equation

HRID 264459 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][N:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[C:13]=3[C:5]=2[CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2=[CH:7][CH:8]=[C:9]3[C:13]([N:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH:11]=[CH:10]3)=[C:5]2[CH:4]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 19036540N-[2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide

Product 1

HCID 19036494HCID 19036494, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

254 mg of N-[2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide were dissolved in 10 ml of dioxane under argon, 238 mg of DDQ were added and the mixture was heated to reflux for 1 hour. Separated crystals were removed by filtration, the filtrate was evaporated and the residue was chromatographed on 50 g of silica gel with methylene chloride/acetone 9:1. 211 mg (83%) of N-[2-(8-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide were obtained as a light yellowish solid. Tlc (silica gel): Rf=0.25 (methylene chloride/acetone 9:1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customSeparated crystals
  4. customwere removed by filtration
  5. customthe filtrate was evaporated
  6. customthe residue was chromatographed on 50 g of silica gel with methylene chloride/acetone 9:1

Sources & evidence

ORD record
ord-1e29e15b130c4e0c920936b6abd4a975
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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