2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 18317249, compound

HRID 1700121Notes

Reaction equation

HRID 1700121 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH:10]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][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.[NH2:39][NH2:40].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CCO>[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C:9]2[N:39]=[N:40][C:12]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])[CH2:15][CH2:14]3)=[CH:11][C:10]=2[C:30]2[CH:35]=[CH:34][N:33]=[CH:32][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 19065063HCID 19065063, compound

Product 1

HCID 18317249HCID 18317249, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under Ar, a solution of 13 (2.2 g, 4.2 mmol) in EtOH (50 mL) was treated with hydrazine (306 mg, 9.6 mmol). After 4 h, the reaction was concentrated to dryness and the residue was partitioned between water-EtOAc (3×). The EtOAc extracts were backwashed with brine, dried, filtered and concentrated to dryness. The residue was dissolved in toluene (60 mL) and 2,3 dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (1.0 g, 4.5 mmol) was added. After 0.5 h, the reaction was chromatographed on a Still column (60 mm) and the product eluted with 90-100% EtOAc-hexanes to yield 1.6 g of 15.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customthe residue was partitioned between water-EtOAc (3×)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue was dissolved in toluene (60 mL)
  7. waitAfter 0.5 h
  8. customthe reaction was chromatographed on a Still column (60 mm)
  9. washthe product eluted with 90-100% EtOAc-hexanes

Sources & evidence

ORD record
ord-e27d268370c6491d8882feac28e680b7
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

Loading…