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1-Chloro-2,4-Dinitrobenzene → 1-(2,4-Dinitrophenyl)-4-[3-(ethyloxy)-4-nitrophenyl]pyridinium chloride

HRID 419513
Notes
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Reaction equation

HRID 419513 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=1[N+:29]([O-:31])=[O:30]>CCO.CC(C)=O>[Cl-:19].[N+:26]([C:23]1[CH:22]=[C:21]([N+:29]([O-:31])=[O:30])[CH:20]=[CH:25][C:24]=1[N+:16]1[CH:15]=[CH:14][C:13]([C:6]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)=[CH:18][CH:17]=1)([O-:28])=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 61-Chloro-2,4-DinitrobenzeneHCID 59452704HCID 59452704, compound

Product 1

HCID 866251941-(2,4-Dinitrophenyl)-4-[3-(ethyloxy)-4-nitrophenyl]pyridinium chlorideYield 92%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Conditions

Temperature
102 °C

Procedure

To 4-[3-(ethyloxy)-4-nitrophenyl]pyridine (2.2 g, 9.0 mmol) in 80 mL of EtOH was added, 1-chloro-2,4-dinitrobenzene (14.6 g, 72.06 mmol). The mixture was heated to 102° C. for 72 h. The mixture was cooled and rotovaped down. The product was taken up in acetone. The resulting slurry was filtered and washed with acetone. The product was dried under vacuum to give the title compound of step B (3.7 g, 7.93 mmol, 92%). MS (ESI): 411 [M+H]+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe resulting slurry was filtered
  3. washwashed with acetone
  4. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-92aab678760d4e8bb6fe6d0cf829ef0e
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093239B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes