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

HRID 419513Notes

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]

Participants

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

temperatureThe mixture was cooled
filtrationThe resulting slurry was filtered
washwashed with acetone
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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