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

HRID 1899968Notes

Reaction equation

HRID 1899968 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH3:12]>C(O)(=O)C.C(O)C.[Fe]>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([Cl:11])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 1

HCID 971552,6-Dichloro-3-nitrotoluene

Product 1

HCID 882822,4-Dichloro-m-toluidineYield 96%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 2,6-dichloro-3-nitrotoluene (50 g) in acetic acid (400 ml) and ethanol (200 ml) was added iron (67.8 g) and the mixture was refluxed for 1.5 hours under nitrogen atmosphere. The insoluble material was filtered off and the filtrate was concentrated. To the residue was added a saturated aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate three times. The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate three times and brine, dried over magnesium sulfate, and concentrated in vacuo to give 2,4-dichloro-3-methylaniline (41 g).

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours under nitrogen atmosphere
  2. filtrationThe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate
  5. extractionthe mixture was extracted with ethyl acetate three times
  6. washThe combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate three times and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40d2c7a00dcd4ed7a9c236fcd75326bf
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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