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

HRID 1485371Notes

Reaction equation

HRID 1485371 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:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[F-].[K+]>C(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][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 78124-ChloroanilineHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 89958N-(4-chlorophenyl)-2-nitroanilineYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 2-fluoronitrobenzene (3.5 g, 24.8 mmol), 4-chlorobenzenamine (3.05 g, 24.0 mmol), K2CO3 (3.45 g, 25.0 mmol) and KF (1.5 g, 25.8 mmol) was heated at 220° C. for 28 min under microwave condition. The solid was dissolved in DCM (150 mL), washed with water (50 mL×3), dried over Na2SO4. The solvent was evaporated in vacuo, and then the mixture was purified by Combi-flash (PE:EA=20:1) to give N-(4-chlorophenyl)-2-nitrobenzenamine (3.2 g, 52%) as a scarlet solid. 1H NMR (300 MHz, CD3OD): δ 6.82-6.87 (m, 1H), 7.27-7.31 (m, 2H), 7.41-7.45 (m, 3H), 7.70-7.73 (m, 1H), 8.15-8.18 (m, 1H).

Workup

  1. washwashed with water (50 mL×3)
  2. dry with materialdried over Na2SO4
  3. customThe solvent was evaporated in vacuo
  4. customthe mixture was purified by Combi-flash (PE:EA=20:1)

Sources & evidence

ORD record
ord-4f4cc1cef61d4d99af7dc88dd1b34207
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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