2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 54398430, compound

HRID 264382Notes

Reaction equation

HRID 264382 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][N:12]([CH2:14][C@@H:15]([NH2:17])[CH3:16])[C:13]=3[C:5]=2[CH:4]=1.C(N(CC)CC)C.[F:27][C:28]([F:35])([F:34])[C:29](OCC)=[O:30].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CO.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2=[CH:7][CH:8]=[C:9]3[C:13]([N:12]([CH2:14][C@@H:15]([NH:17][C:29](=[O:30])[C:28]([F:35])([F:34])[F:27])[CH3:16])[CH:11]=[CH:10]3)=[C:5]2[CH:4]=1

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 3045241Ro 60-0241

Product 1

HCID 54398430HCID 54398430, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.5 g of (S)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethylamine, 0.74 g of triethylamine and 1.04 g of ethyl trifluoroacetate in 100 ml of anhydrous methanol was stirred at room temperature for 27 hours. After the solvent had been drawn off in a vacuum, the residue was taken up with 100 ml of ahydrous dioxane, 1.56 g of DDQ were added and the mixture was boiled under reflux for 1.5 hours. Subsequently, the reaction mixture was concentrated in a vacuum and the residue was purified by column chromatography on silica gel (dichloromethane/acetone 4:1). 1.2 g (59%) of (S)-N-[2-(8-methoxy-1H-benz[g]indol-1-yl)-1-methyl-ethyl]-trifluoracetamide were obtained as a pale brown solid which was used in the next reaction without additional recrystallization.

Workup

  1. additionwere added
  2. temperatureunder reflux for 1.5 hours
  3. concentrationSubsequently, the reaction mixture was concentrated in a vacuum
  4. customthe residue was purified by column chromatography on silica gel (dichloromethane/acetone 4:1)

Sources & evidence

ORD record
ord-d7f92be426dd4adbb9eee490d9f9e823
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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