Chlorine → 3-Chloro-4-cyclohexylaniline

HRID 1900087Notes

Reaction equation

HRID 1900087 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C2C=CC=CC=2[N+]([O-])=O)CCCCC1.[Cl:31]Cl.[BH4-].[K+]>[Fe](Cl)(Cl)Cl.[Cu]Cl.O>[Cl:31][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:7]=1[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[NH2:13]

Participants

8

Reactant 4

HCID 24526ChlorineHCID 795641-Cyclohexyl-4-nitrobenzeneHCID 138940Benzene, 1-cyclohexyl-2-nitro-HCID 4192641Potassium borohydride

Product 1

HCID 233718813-Chloro-4-cyclohexylaniline

Reagents, catalysts & solvents 3

HCID 24380Iron chloride (FeCl3)CatalystHCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 1.0 g (5 mmol) of 4-cyclohexyl-nitrobenzene and 0.1 g of iron(III) chloride was heated to 60°. After the cyclohexyl-nitrobenzene had melted chlorine gas was conducted through the well-stirred mixture for 15 minutes. Then, 20 ml of ice-water were added and the mixture was extracted with ether. The ether was distilled off and the residue was dissolved in 60 ml of methanol. Then, the solution was treated with 2.5 g (25 mmol) of copper(I) chloride and portionwise with 1.6 g (29 mmol) of potassium borohydride. After stirring for 30 minutes the mixture was poured into 0.5 l of water and extracted with ether. Drying over sodium sulfate, distillation of the ether and chromatography over silica gel with hexane/ethyl acetate 9:1 gave 0.68 g of oil. MS: m/e (% basic peak)=209 (M+, 75), 166 (100), 140 (78), 131 (62).

Workup

  1. temperaturewas heated to 60°
  2. extractionthe mixture was extracted with ether
  3. distillationThe ether was distilled off
  4. dissolutionthe residue was dissolved in 60 ml of methanol
  5. extractionextracted with ether
  6. dry with materialDrying over sodium sulfate, distillation of the ether and chromatography over silica gel with hexane/ethyl acetate 9:1

Sources & evidence

ORD record
ord-e6ee508f656e4cea973c3e1744cd5024
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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