1-Chloro-2,4-Dinitrobenzene → Pyridinium, 1-(2,4-dinitrophenyl)-, chloride (1:1)

HRID 257645Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C>C(O)C>[Cl-:1].[N+:11]([C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N+:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

Conditions

Temperature: 30 °C

Procedure

1-Chloro-2,4-dinitrobenzene (10 g, 49.4 mmol) and pyridine (40 ml, 495 mmol) were mixed in a 100 ml round-bottom flask; the resultant solution turned orange and became very cold. The flask was then warmed to 30° C, by which time the solution was dark brown, and the solution was left to react overnight. The resulting solid was broken up, washed with ether and collected on a fritted glass funnel to yield 12.3 g of a pale pink, semicrystalline solid. This solid was dissolved in 120 ml of hot ethanol, and the resultant solution decolorized with charcoal and filtered. The crystals obtained were washed with a 1:1 v/v ethanol:ether mixture. A second crop of crystals was collected and combined with the first crop, to give an overall yield of 70% of theoretical.

Workup

waitthe solution was left
customto react overnight
washwashed with ether
customcollected on a fritted glass funnel
customto yield 12.3 g of a pale pink, semicrystalline solid
filtrationfiltered
customThe crystals obtained
washwere washed with a 1:1 v/v ethanol
customA second crop of crystals was collected
customto give an overall yield of 70% of theoretical

Sources & evidence

ORD record: ord-af552d20dbbe4ceaa248828a2ade55fa
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262549

Reaction notes

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