2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 70101852, compound

HRID 1700123Notes

Reaction equation

HRID 1700123 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH:10]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([F:36])[CH:31]=2)[CH2:11][C:12](=O)[CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)[CH:6]=[CH:7][CH:8]=1.[NH2:40][NH2:41].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CCO>[F:38][C:2]([F:39])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[N:40]=[N:41][C:12]([CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])[CH2:17][CH2:18]3)=[CH:11][C:10]=2[C:30]2[CH:35]=[CH:34][N:33]=[C:32]([F:36])[CH:31]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 9321HydrazineHCID 18317238HCID 18317238, compound

Product 1

HCID 70101852HCID 70101852, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under Ar, a solution of 19 (8.8 g, 14.1 mmol) in EtOH (270 mL) was stirred at room temperature and treated with hydrazine (1.4 g, 42.1 mmol). After 2 h, the reaction was concentrated to dryness. The reaction was partitioned between H2O and EtOAc (3×). The organic extracts were backwashed with brine, dried, filtered and concentrated to dryness. The residue was dissolved in toluene (400 mL) and treated with DDQ (3.4 g, 14.9 mmol). After stirring at room temperature for 3 h, the reaction was concentrated to dryness. The residue was chromatographed on a Still column (100 mm) and the product eluted with 60% EtOAc-hexanes to yield 5.5 g of 20.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customThe reaction was partitioned between H2O and EtOAc (3×)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue was dissolved in toluene (400 mL)
  7. concentrationthe reaction was concentrated to dryness
  8. customThe residue was chromatographed on a Still column (100 mm)
  9. washthe product eluted with 60% EtOAc-hexanes

Sources & evidence

ORD record
ord-1c7e1d1cf9474b53b2e687bff0b2f6d1
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

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