1-Chloro-2-nitrobenzene → N-cyclohexyl-2-nitroaniline

HRID 1081260Notes

Reaction equation

HRID 1081260 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>C1(N)CCCCC1.[Cu]I>[CH:3]1([NH:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:2]1

Participants

5

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 3101179N-cyclohexyl-2-nitroanilineYield 164.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7965CyclohexylamineSolvent

Procedure

A mixture of 2-chloronitrobenzene (20 g), potassium carbonate (35 g) and copper (I) iodide (1.21 g)in cyclohexylamine (43.6 ml) was heated at 150° under nitrogen for 18 h. The mixture was allowed to cool to room temperature and was adsorbed onto silica. This was chromatographed with hexane-EA (98:2) as eluent to give the title compound (22.94 g) as an orange solid.

Workup

  1. temperaturewas heated at 150° under nitrogen for 18 h
  2. customThis was chromatographed with hexane-EA (98:2) as eluent

Sources & evidence

ORD record
ord-d5f6dc4028b845bfb81b9287b1ee1aa2
Source dataset
uspto-grants-1996_12
Patent number
US05585376

Reaction notes

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