2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → DIMETHYL 1,4,6,11-TETRAPROPYLNAPHTHACENE-2,3-DICARBOXYLATE

HRID 600130Notes

Reaction equation

HRID 600130 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH2:15]([C:18]1[C:35]2[CH2:34][C:33]3[C:24](=[C:25]([CH2:39][CH2:40][CH3:41])[C:26]4[C:31]([C:32]=3[CH2:36][CH2:37][CH3:38])=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:23][C:22]=2[C:21]([CH2:42][CH2:43][CH3:44])=[C:20]([C:45]([O:47][CH3:48])=[O:46])[C:19]=1[C:49]([O:51][CH3:52])=[O:50])[CH2:16][CH3:17]>O1CCOCC1>[CH2:15]([C:18]1[C:35]2[C:22](=[CH:23][C:24]3[C:33]([CH:34]=2)=[C:32]([CH2:36][CH2:37][CH3:38])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]=3[CH2:39][CH2:40][CH3:41])[C:21]([CH2:42][CH2:43][CH3:44])=[C:20]([C:45]([O:47][CH3:48])=[O:46])[C:19]=1[C:49]([O:51][CH3:52])=[O:50])[CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11477816HCID 11477816, compound

Product 1

HCID 11156527DIMETHYL 1,4,6,11-TETRAPROPYLNAPHTHACENE-2,3-DICARBOXYLATEYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,3-Dichloro-5,6-dicyanobenzoquinone (0.050 g, 0.22 mmol) was added to a solution of dimethyl 5,12-dihydro-1,4,6,11-tetrapropylnaphthacene-2,3-dicarboxylate (0.103 g, 0.2 mmol) in 1,4-dioxane (5 ml). Subsequently, the mixture was refluxed for 3 hours. After filtration, the solvent in the mixture was removed in vacuum. Chloroform was added and the mixture was again filtered. Recrystallization from chloroform/methanol gave 0.076 g of the title compound as red needle-like crystals. The NMR yield was 97% and the isolated yield was 71%. The X-ray crystal structure analysis of the title compound is show in FIG. 4

Workup

  1. temperatureSubsequently, the mixture was refluxed for 3 hours
  2. filtrationAfter filtration
  3. customthe solvent in the mixture was removed in vacuum
  4. additionChloroform was added
  5. filtrationthe mixture was again filtered
  6. customRecrystallization from chloroform/methanol

Sources & evidence

ORD record
ord-691dad9e62944cb69700db3fc7ea9f31
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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