2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19420953, compound

HRID 864068Notes

Reaction equation

HRID 864068 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]=[N:11][N:12]([CH2:14][CH: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][CH:15]([NH:17][C:29](=[O:30])[C:28]([F:35])([F:34])[F:27])[CH3:16])[N: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 30452301-(8-Methoxy-4,5-dihydro-1H-benzo[g]indazol-1-yl)propan-2-amine

Product 1

HCID 19420953HCID 19420953, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.86 g (3.34 mmol) of (RS)-2-(4,5-dihydro-8-methoxy-1H-benz[g]indazol-1-yl)-1-methyl-ethylamine, 0.56 ml (4 mmol) of triethylamine and 0.56 ml (4 mmol) of ethyl trifluoroacetate in 60 ml of anhydrous methanol was stirred at room temperature for 50 hours. After removing the solvent in a vacuum, the residue was taken up with 70 ml of anhydrous dioxan, 0.8 g (3.5 mmol) of DDQ was added and the mixture was boiled under reflux for 3 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). 0.97 g (82%) of (RS)-N-[2-(8-methoxy-1H-benz[g]indazol-1-yl)-1-methyl-ethyl]-trifluoroacetamide was obtained as a pale brown solid which was used in the next reaction without further recrystallization.

Workup

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

Sources & evidence

ORD record
ord-6ee76be9e2bd4c2d99f1c8a582792b78
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

Loading…