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Pyridine → 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethane-1,2-dione

HRID 1392124
Notes
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Reaction equation

HRID 1392124 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[O:10])=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-:25][Cr](Cl)(=O)=O.N1C=CC=CC=1>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[O:10])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 219848672-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)ethan-1-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 220660771-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)ethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

2-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)ethanone (2.7 g, 9.01 mmol) was dissolved in 1,2-dichloroethane (25 ml) and freshly made PCC (3.89 g, 18.02 mmol), pyridine (1.43 g, 18.02 mmol) and molecular sieves were added. The reaction mixture was refluxed under inert atmosphere overnight. The solution was cooled to 25° C., filtered through Silica and then solvent was evaporated under reduced pressure. The crude product (1.9 g, 66%) was used directly in the next step. 1H NMR (500 MHz) δ 7.97 (d, 2H), 7.84 (d, 1H), 7.52 (d, 2H), 7.46 (s, 1H), 7.44 (d, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed under inert atmosphere overnight
  2. filtrationfiltered through Silica
  3. customsolvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3cbb9601a1ed43258aaa8f322aa5f853
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07342019B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes