Hydrochloric Acid → N-(4-chlorophenyl)-2-nitroaniline

HRID 1019845Notes

Reaction equation

HRID 1019845 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.[F-].[K+].Cl>C(Cl)Cl>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 738951-Fluoro-2-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 89958N-(4-chlorophenyl)-2-nitroanilineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2-fluoro-nitrobenzene (33.7 g), 4-chloroaniline (61.0 g) and anhydrous potassium fluoride (13.9 g) was stirred at 180° C. for 10 h. After being cooled to rt, 3 M HCl was added and the mixture was stirred at 100° C. for 30 min. Then cooled to rt, filtered by suction, washed with water to give a brown solid. The solid was dissolved in CH2Cl2 and filtered through a thin pad of silica gel, washed with CH2Cl2. The filtrate was concentrated to dryness, and the residue was recrystallized with 95% ethanol to give 57.0 g of orange solid.

Workup

  1. temperatureAfter being cooled to rt
  2. stirringthe mixture was stirred at 100° C. for 30 min
  3. temperatureThen cooled to rt
  4. filtrationfiltered by suction
  5. washwashed with water
  6. customto give a brown solid
  7. filtrationfiltered through a thin pad of silica gel
  8. washwashed with CH2Cl2
  9. concentrationThe filtrate was concentrated to dryness
  10. customthe residue was recrystallized with 95% ethanol

Sources & evidence

ORD record
ord-a4d1081b12b345bab372c503d5def2e2
Source dataset
uspto-grants-2014_05
Patent number
US08716292B2

Reaction notes

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