2-Chloro-3-nitrotoluene → 2-Chloro-m-toluidine

HRID 1107438Notes

Reaction equation

HRID 1107438 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11]>CCO.CCOC(C)=O.[Pt]>[Cl:1][C:2]1[C:3]([CH3:11])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 1

HCID 775912-Chloro-3-nitrotoluene

Product 1

HCID 114124382-Chloro-m-toluidine

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-3-nitrotoluene (1.0 g, 5.8 mmol) and 5% platinum-on-carbon (0.1 g) in 25 ml of EtOH was reacted overnight at room temperature and 60 psi. The reaction mixture was filtered and the filtrate concentrated in vacuo to provide an oil. This oil was dissolved in EtOAc, washed with H2O, dried over Na2SO4, filtered and then concentrated in vacuo.

Workup

  1. customwas reacted overnight at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto provide an oil
  5. washwashed with H2O
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-854fa90d0f8b4c13845bc7c8b4ba4ae7
Source dataset
uspto-grants-2000_05
Patent number
US06060484

Reaction notes

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