4-(4-Chlorophenyl)-3-nitropyridine → HCID 21947116, compound

HRID 47189Notes

Reaction equation

HRID 47189 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[CH:4][CH:3]=1>O.C(O)(=O)C.C(O)CC.C(OC(=O)C)C.[Fe]>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

7

Reactant 1

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

Product 1

HCID 21947116HCID 21947116, compound

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a sulfonation flask 8.4 g (36 mmol) 4(4′chlorophenyl)3-nitropyridine is dissolved in a mixture of 100 ml water, 35 ml acetic acid and 10 ml n-propanol. After the addition of 7.0 g (125 mmol) iron powder, the mixture is heated for 3 hours under reflux conditions. After cooling to room temperature the mixture is diluted with ethylacetate and filtered over hyflo. Then the filtrate is neutralized by the addition of sodiumbicarbonate solution and the organic phase separated. The water phase is extracted twice with ethylacetate and the combined organic phases dried over sodium sulfate. After distilling off the solvent in a water jet vacuum the obtained raw material is purified by column chromatography over silica gel (eluant ethylacetate). Yield: 3.9 g 3-amino-4-(4′chlorophenyl)pyridine in the form of a slightly brownish powder, m.p.: 144-146° C.

Workup

  1. temperaturethe mixture is heated for 3 hours under reflux conditions
  2. filtrationfiltered over hyflo
  3. additionThen the filtrate is neutralized by the addition of sodiumbicarbonate solution
  4. customthe organic phase separated
  5. extractionThe water phase is extracted twice with ethylacetate
  6. dry with materialthe combined organic phases dried over sodium sulfate
  7. distillationAfter distilling off the solvent in a water jet vacuum the
  8. customobtained raw material
  9. customis purified by column chromatography over silica gel (eluant ethylacetate)

Sources & evidence

ORD record
ord-b8941b0391c44f3a9113f97f00ae3490
Source dataset
uspto-grants-2004_03
Patent number
US06699818B1

Reaction notes

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