Water → N-(4-chlorophenyl)-2-nitroaniline

HRID 2185933Notes

Reaction equation

HRID 2185933 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.O>N1C=CC=CC=1>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 78124-ChloroanilineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 89958N-(4-chlorophenyl)-2-nitroanilineYield 51.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

2-Fluoronitrobenzene (3.0 g) and 4-chloroaniline (2.5 g) were dissolved in pyridine (30 ml) and stirred at 80° C. for 18 hours. The resultant solution was allowed to cool, and thereafter, water (100 ml) was added thereto and the mixture was extracted with ethyl acetate (50 ml×3). The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was re-crystallized from ethyl acetate-hexane, to thereby yield the target compound (2.5 g) as pale-brown crystals.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate (50 ml×3)
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was re-crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c6f2b0ea96274016a81c205f982574d3
Source dataset
uspto-grants-2002_06
Patent number
US06403607B1

Reaction notes

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