2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 66940495, compound

HRID 1844996Notes

Reaction equation

HRID 1844996 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[CH:11][CH:12]=2)[CH2:7][NH:6]1)=[O:4].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=2)=[O:4]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 53635299HCID 53635299, compound

Product 1

HCID 66940495HCID 66940495, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the above ester in 1,4-dioxane (100 mL) was added 2.8 g (12.7 mmol) of DDQ, and the reaction mixture was refluxed for 6 h. After removal of solvents, the residue was dissolved with ethyl acetate (250 mL) and washed with aq. NaHSO3 solution (1M solution, 100 mL), water and brine. The ethyl acetate layer was dried over sodium sulfate, evaporated under reduced pressure and purified by column chromatography (eluting with ethyl acetate then EtOAc/methanol v/v=100:5) to provide 1.0 g (71%) of the 7-nitro-isoquinoline-3-carboxylic acid methyl ester. LCMS: 233 (M+1)+. The methyl ester was hydrolyzed according to the general procedure B to give 0.9 of 7-nitro-isoquinoline-3-carboxylic acid. LCMS: 219 (M+1)+.

Workup

  1. temperaturethe reaction mixture was refluxed for 6 h
  2. customAfter removal of solvents
  3. dissolutionthe residue was dissolved with ethyl acetate (250 mL)
  4. washwashed with aq. NaHSO3 solution (1M solution, 100 mL), water and brine
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. custompurified by column chromatography (
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1a88fd80910d44ddabf265b43bd9a437
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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