2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 22249620, compound

HRID 966035Notes

Reaction equation

HRID 966035 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[CH2:15]([CH:17]([N:20]1[C:28]2[N:27]3[N:29]=[C:30]([CH3:34])[C:31]([CH:32]=O)=[C:26]3[N:25]=[C:24]([CH3:35])[C:23]=2[CH2:22][CH2:21]1)[CH2:18][CH3:19])[CH3:16].[C:36]1([NH2:43])[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH2:42].[OH-].[Na+]>C(#N)C>[NH:42]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:43]=[C:32]1[C:31]1[C:30]([CH3:34])=[N:29][N:27]2[C:28]3[N:20]([CH:17]([CH2:18][CH3:19])[CH2:15][CH3:16])[CH2:21][CH2:22][C:23]=3[C:24]([CH3:35])=[N:25][C:26]=12

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 7243O-PhenylenediamineHCID 14798Sodium HydroxideHCID 22249649HCID 22249649, compound

Product 1

HCID 22249620HCID 22249620, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

DDQ (79 mg, 0.35 mmol) was added to a solution of 8-(1-ethylpropyl)-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-3-carbaldehyde (100 mg, 0.35 mmol) and 1,2-phenylenediamine (40 mg, 0.37 mmol) in acetonitrile (1 mL) at room temperature and the mixture was stirred for one day. Further, a 0.5N aqueous solution of sodium hydroxide was added thereto, followed by stirring for five hours. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by dry pack silica gel column chromatography (50% ethyl acetate/hexane), to give the title compound (23 mg) as pale yellow crystals.

Workup

  1. stirringby stirring for five hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified
  6. dry with materialby dry pack silica gel column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e333226e6ece4001973ebb11b43ddcd3
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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