Cyclohexene → 4-Chloro-2-methyl-3-nitroaniline

HRID 1106719Notes

Reaction equation

HRID 1106719 reaction equation
[Cl:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH3:11])[C:5]([N+:8]([O-])=O)=[CH:6][CH:7]=1.C1CCCCC=1>[Pd].C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 52489471-Chloro-3-methyl-2,4-dinitrobenzene

Product 1

HCID 187897374-Chloro-2-methyl-3-nitroaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-chloro-2,6-dinitrotoluene (18.0 g), cyclohexene (51 mL), and 10% palladium on charcoal (4.5 g) in ethanol (350 mL) was heated at reflux under an atmosphere of nitrogen for 1.5 hr. The reaction mixture was cooled to room temperature, filtered through celite, then evaporated under reduced pressure. The residue was dissolved in ethyl ether and filtered through a short silica column. Evaporation of the ether afforded 14.8 g as an orange solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of nitrogen for 1.5 hr
  3. filtrationfiltered through celite
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl ether
  6. filtrationfiltered through a short silica column
  7. customEvaporation of the ether
  8. customafforded 14.8 g as an orange solid

Sources & evidence

ORD record
ord-1e9dc11f926b492ca7173c404ef83f33
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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