2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Diethyl 2,6-diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarboxylate

HRID 324793Notes

Reaction equation

HRID 324793 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH2:15]([O:17][C:18]([C:20]1[CH:25]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[C:24]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:23]([CH:38]([CH3:40])[CH3:39])[NH:22][C:21]=1[CH:41]([CH3:43])[CH3:42])=[O:19])[CH3:16]>C(Cl)Cl>[CH2:15]([O:17][C:18]([C:20]1[C:21]([CH:41]([CH3:43])[CH3:42])=[N:22][C:23]([CH:38]([CH3:40])[CH3:39])=[C:24]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:25]=1[C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)=[O:19])[CH3:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11661355Diethyl 1,4-dihydro-2,6-diisopropyl-4-(4-fluorophenyl)pyridine-3,5-dicarboxylate

Product 1

HCID 10179180Diethyl 2,6-diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.8 g (16.4 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone is added to a solution of 6.6 g (16.4 mmol) of 1,4-dihydro-2,6-diisopropyl-4-(4-fluorophenyl)pyridine-3,5-dicarboxylic acid diethylester in 200 ml of analysis grade methylene chloride, and the mixture is then stirred for 1 h at room temperature. After this, it is drawn off by suction over diatomaceous earth, and the methylene chloride phase is extracted 3 times with 100 ml of water each time and dried on magnesium sulfate. After concentrating in a vacuum, the residue is chromatographed on a column (100 g of silica gel, 70-230 mesh, diameter 3.5 cm, with ethyl acetate/petroleum ether 1:9).

Workup

  1. extractionthe methylene chloride phase is extracted 3 times with 100 ml of water each time
  2. customdried on magnesium sulfate
  3. concentrationAfter concentrating in a vacuum
  4. customthe residue is chromatographed on a column (100 g of silica gel, 70-230 mesh, diameter 3.5 cm, with ethyl acetate/petroleum ether 1:9)

Sources & evidence

ORD record
ord-90af336a967f4114be33526c4c58f3a3
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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