Potassium Carbonate → 2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]-3-nitropyridine

HRID 2230965Notes

Reaction equation

HRID 2230965 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[C:14](/[CH:18]=[CH:19]/[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[N+:8]([C:7]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](/[CH:18]=[CH:19]/[C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 157868883-[(E)-2-(3-aminophenyl)vinyl]pyridine

Product 1

HCID 227244742-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]-3-nitropyridineYield 25.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (1.15 g), 3-[(E)-2-(3-aminophenyl)vinyl]pyridine (1.23 g) and potassium carbonate (1.1 g) in 1,4-dioxane (15 ml) was stirred under reflux for 22 hours. After cooling, insoluble materials were removed by filtration and the filtrate was concentrated. The residue was chromatographed on silica gel column (2% methanol in chloroform) to give 3-nitro-2-[3-[(E)-2-(3-pyridyl)vinyl]phenylamino]pyridine (510 mg) as an orange solid.

Workup

  1. temperatureunder reflux for 22 hours
  2. temperatureAfter cooling
  3. custominsoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe residue was chromatographed on silica gel column (2% methanol in chloroform)

Sources & evidence

ORD record
ord-71fc17e278f14fb6aa52b83a462cd20b
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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