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

HRID 2423308Notes

Reaction equation

HRID 2423308 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 (2.46 g, 9.5 mmol), cyclohexene (10 mL) and 10% palladium on charcoal (0.6 g) in ethanol (50 mL) was heated at reflux under an atmosphere of nitrogen for 2 h. After this time the reaction mixture was cooled to room temperature, filtered through celite and then evaporated under reduced pressure. The residue was dissolved in diethyl ether and filtered through a short silica column. Evaporation of the ether afforded the product as an orange solid. 1H NMR (400 MHz) (CDCl3) δ 7.15 (d, J=8.7 Hz, 1H); 6.72 (d, J=8.7 Hz, 1H); 3.80 (bs, 2H); 2.11 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under an atmosphere of nitrogen for 2 h
  3. filtrationfiltered through celite
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in diethyl ether
  6. filtrationfiltered through a short silica column
  7. customEvaporation of the ether

Sources & evidence

ORD record
ord-d2572aeff3df47d5a7f1bfca0b311050
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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