2,6-Dichloro-3-nitrotoluene → 2,4-Dichloro-m-toluidine

HRID 6677

Reaction equation

HRID 6677 reaction equation
Cl[Sn]Cl.O.[Cl:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[CH3:16]>C(O)C>[Cl:5][C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[CH3:16]

Participants

4

Reactant 2

HCID 971552,6-Dichloro-3-nitrotolueneHCID 43835034Tin dichloride dihydrate

Product 1

HCID 882822,4-Dichloro-m-toluidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of SnCl2.H2O (140 g, 0.62 mol) in ethanol (350 mL) was added a solution of 2,6-dichloro-3-nitrotoluene (25 g, 0.12 mol) in ethanol (50 mL). The reaction mixture was refluxed for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (100 mL), pH was adjusted to approximately pH 12 with 1N NaOH solution and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate, and concentrated to afford 2,6-dichloro-3-aminotoluene (21 g, 98%); NMR (CDCl3) 2.42 (s, 3), 6.62 (d, 1), 7.14 (d, 1) ppm.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water (100 mL)
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c78937719c06435bb816f877129f639e
Source dataset
uspto-grants-2006_08
Patent number
US07084142B2

Linked notes

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