Potassium Carbonate → HCID 22724408, compound

HRID 2086805Notes

Reaction equation

HRID 2086805 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]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOCCOC>[N+:8]([C:7]1[C:2]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=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 4595173-(2-Pyridyl)aniline

Product 1

HCID 22724408HCID 22724408, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-3-nitropyridine (1.15 g), 2-(3-aminophenyl)pyridine (1.12 g) and potassium carbonate (1.36 g) in diglyme (15 ml) was stirred at 150° C. for 3 hours. After cooling, insoluble materials were removed by filtration and the filtrate was concentrated. The residue was chromatographed on silica gel column (hexane-ethyl acetate, 1:1) to give 3-nitro-2-[3-(2-pyridyl)phenylamino]pyridine (1.68 g)

Workup

  1. temperatureAfter cooling
  2. custominsoluble materials were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was chromatographed on silica gel column (hexane-ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-2322878b0eaf4b73b48b9241eda809e6
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

Loading…