Chlorobenzene → 3-Chloro-4-(4-chlorophenyl)benzenamine

HRID 1885514Notes

Reaction equation

HRID 1885514 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1N.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1.[Cl:1][C:2]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:3]=1[C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 7964ChlorobenzeneHCID 84922-Chloro-4-nitroaniline

Product 2

HCID 198789103-Chloro-4-(4-chlorophenyl)benzenamineYield 98%HCID 198789172,4'-Dichloro-4-nitro-biphenyl

Conditions

Temperature
120 °C

Procedure

2,4'-dichloro-4-nitro-biphenyl was prepared by dissolving 2-chloro-4-nitroaniline (2.6 g, 15 mmol) in chlorobenzene (20 mL, 200 mmol), heated to 120° C. under a nitrogen atmosphere. i-Amylnitrite (3.4 mL, 25 mmol) was added to the solution slowly over 1 h via a syringe pump and canula. After stirring for 12 h the reaction mixture was cooled to ambient temperature and the excess chlorobenzene was removed in vacuo. The residue after evaporation was chromatographed by filtration through silica gel as in Example 1A, using mixture of hexane and ethyl acetate (80:20) as the eluent. Further purification was achieved by chromatography [Chromatotron®, 4 mm silica gel, hexanes/methylene chloride, 80:20, 20 mL/min] which yielded the title compound (1.75 g). Mass spectrum: m/z at 267 for C12H7Cl2NO2.

Workup

  1. temperaturewas cooled to ambient temperature
  2. customthe excess chlorobenzene was removed in vacuo
  3. customThe residue after evaporation
  4. filtrationwas chromatographed by filtration through silica gel as in Example 1A
  5. additionmixture of hexane and ethyl acetate (80:20) as the eluent
  6. customFurther purification

Sources & evidence

ORD record
ord-365c21eefc5c468397b8e1893e8c8150
Source dataset
uspto-grants-1992_09
Patent number
US05145790

Reaction notes

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