Potassium Carbonate → 4-(4-Chlorophenyl)-3-nitropyridine

HRID 2214339Notes

Reaction equation

HRID 2214339 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 219471174-(4-Chlorophenyl)-3-nitropyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a sulfonation flask 6.9 g (44 mmol) of 4-chloro-3-nitropyridine, 6.5 g (42 mmol) 4-chloro-phenylboronic acid, 6.0 g (44 mmol) potassium carbonate (saturated solution in water) and 1.0 g (0.9 mmol) tetrakis(triphenylphosphine)palladium are dissolved in 100 ml of dimethoxyethane (DME). The mixture is heated under reflux conditions under a constant nitrogen stream for 5 hours. Then the solvent is removed in a water jet vacuum and the residue taken up in ethylacetate. The organic phase is washed twice with water and after drying of the organic phase with sodium sulfate, the solvent is removed in a water jet vacuum. The resulting crude product is purified by column chromatography over silica gel (eluant: hexane/ethylacetate 1:1). Yield: 8.9 g 4-(4′-chlorophenyl)-3-nitropyridine in the form of brownish crystals; m.p. 74–76° C.

Workup

  1. temperatureThe mixture is heated under reflux conditions under a constant nitrogen
  2. customThen the solvent is removed in a water jet vacuum
  3. washThe organic phase is washed twice with water
  4. dry with materialafter drying of the organic phase with sodium sulfate
  5. customthe solvent is removed in a water jet vacuum
  6. customThe resulting crude product is purified by column chromatography over silica gel (eluant: hexane/ethylacetate 1:1)

Sources & evidence

ORD record
ord-a17dce72e04f4cf88382b071102640a5
Source dataset
uspto-grants-2006_09
Patent number
US07109150B2

Reaction notes

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