3-Chloro-5-nitrotoluene → 3-Chloro-5-methylaniline

HRID 1517969Notes

Reaction equation

HRID 1517969 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[Sn].O.O.[Cl-].[Cl-]>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:11])[CH:3]=1)[NH2:8]

Participants

5

Reactant 2

HCID 2978873-Chloro-5-nitrotolueneHCID 131729857Tin dichloride-dihydrate

Product 1

HCID 124754343-Chloro-5-methylaniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.4 g of 3-chloro-5-nitro-toluene are dissolved in 35 ml of ethanol, combined with 15.8 g tin dichloride-dihydrate and refluxed for 3 hours. The solvent is eliminated in vacuo, the residue is taken up in 4 M sodium hydroxide solution and filtered through kieselguhr. The filter cake is washed thoroughly with ethyl acetate. The aqueous phase is extracted 3 times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution and dried on magnesium sulphate. The solvent is eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 81:15 to 70:30).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationfiltered through kieselguhr
  3. washThe filter cake is washed thoroughly with ethyl acetate
  4. extractionThe aqueous phase is extracted 3 times with ethyl acetate
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. customdried on magnesium sulphate
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 81:15 to 70:30)

Sources & evidence

ORD record
ord-8ba689a804ec4c51a97fd6a969edc167
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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