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

HRID 1073106Notes

Reaction equation

HRID 1073106 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH:15]([C:18]1[NH:19][C:20]([CH:41]([CH3:43])[CH3:42])=[C:21]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:22]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:17])[CH3:16]>C(Cl)Cl>[CH:41]([C:20]1[C:21]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:22]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:18]([CH:15]([CH3:17])[CH3:16])[N:19]=1)([CH3:43])[CH3:42]

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 are added to a solution of 6.6 g (16.4 mmol) of the compound from Example 2 in 200 ml of methylene chloride p.a. and the mixture is stirred for 1 h at room temperature. It is then filtered over kieselgur with suction, the methylene chloride phase is extracted three times using 100 ml of water each time and dried over magnesium sulphate. After concentrating in vacuo, the residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ 3.5 cm, using ethyl acetate/petroleum ether (1:9).

Workup

  1. filtrationIt is then filtered over kieselgur with suction
  2. extractionthe methylene chloride phase is extracted three times
  3. dry with materialdried over magnesium sulphate
  4. concentrationAfter concentrating in vacuo
  5. customthe residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ 3.5 cm

Sources & evidence

ORD record
ord-0bbc69643d93481ca8d479bc0ec7d871
Source dataset
uspto-grants-1990_11
Patent number
US04968689

Reaction notes

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