1,3-Dichloro-4-methoxy-2-nitrobenzene → 2,6-Dichloro-3-methoxyaniline

HRID 1902866Notes

Reaction equation

HRID 1902866 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([Cl:11])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]>C(O)C.[Ni]>[Cl:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][CH:5]=[C:6]([Cl:11])[C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 205138861,3-Dichloro-4-methoxy-2-nitrobenzene

Product 1

HCID 205138882,6-Dichloro-3-methoxyaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 62.4 g of 2,4-dichloro-3-nitroanisole in 750 ml of ethanol is treated with 19 g of Raney-nickel and hydrogenated for 8 hours. The obtained solution is filtered and evaporated in vacuo. The residue is taken up in methylene chloride and the solution is washed with a dilute sodium carbonate solution. After drying the organic phase over sodium sulfate and evaporating in vacuo, there is obtained 2,6-dichloro-3-methoxyaniline of boiling point 84° (0.1 Torr).

Workup

  1. filtrationThe obtained solution is filtered
  2. customevaporated in vacuo
  3. washthe solution is washed with a dilute sodium carbonate solution
  4. dry with materialAfter drying the organic phase over sodium sulfate
  5. customevaporating in vacuo

Sources & evidence

ORD record
ord-1c159d2265fd45d0afddb341e4d04751
Source dataset
uspto-grants-1982_12
Patent number
US04366160

Reaction notes

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