2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 22005043, compound

HRID 324792Notes

Reaction equation

HRID 324792 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:8]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[NH:10][C:11]=1[CH2:12][CH3:13])=[O:5])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:8]([C:19]([O:21][CH3:22])=[O:20])[C:9]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)=[N:10][C:11]=1[CH2:12][CH3:13])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22004876HCID 22004876, compound

Product 1

HCID 22005043HCID 22005043, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 g (6.98 mmol) of 1,4-dihydro-2-cyclopentyl-6-ethyl-4-(4-fluorophenyl)pyridine-3,5-dicarboxylic acid-3-methylester-5-ethylester is dissolved in 100 ml of absol. methylene chloride, and after addition of 1.6 g (6.98 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), the mixture is stirred for 1 hour at room temperature. After this, it is drawn off by suction over diatomaceous earth and concentrated in a vacuum. The residue is chromatographed over silica gel (100 g of silica gel, 230-400 mesh, d 3.5 cm, mobile solvent ethyl acetate/petroleum ether 5:95).

Workup

  1. concentrationconcentrated in a vacuum
  2. customThe residue is chromatographed over silica gel (100 g of silica gel, 230-400 mesh, d 3.5 cm, mobile solvent ethyl acetate/petroleum ether 5:95)

Sources & evidence

ORD record
ord-3d2b922b8447411ba3aedbd54dc243e6
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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