1-Chloro-2,4-Dinitrobenzene → 1-(2,4-Dinitrophenyl)-4,4'-bipyridinium chloride

HRID 230975

Reaction equation

HRID 230975 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]>C(O)C>[Cl-:13].[N+:20]([C:17]1[CH:16]=[C:15]([N+:23]([O-:25])=[O:24])[CH:14]=[CH:19][C:18]=1[N+:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][NH+:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1)([O-:22])=[O:21].[Cl-:13]

Participants

4

Reactant 2

HCID 61-Chloro-2,4-DinitrobenzeneHCID 111074,4'-Bipyridine

Product 1

HCID 230213161-(2,4-Dinitrophenyl)-4,4'-bipyridinium chlorideYield 136.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,4′-Bipyridine (10 g, 0.065 moles) and chloro-2,4-dinitrobenzene (13 g, 0.065 moles) in ethanol (150 ml) in a 250 ml flask were refluxed for fifteen hours and allowed to cool. The ethanol was removed under vacuum and acetone (200 ml) was added and the mixture was stirred. The suspension was filtered and dried under vacuum to yield 1-(2,4-dinitrophenyl)-4,4′-bipyridinium chloride (17.5 g).

Workup

  1. temperatureto cool
  2. customThe ethanol was removed under vacuum and acetone (200 ml)
  3. additionwas added
  4. filtrationThe suspension was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d710617f6b1049eeb68c0d3e7101fa67
Source dataset
uspto-grants-2009_07
Patent number
US07567371B2

Linked notes

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