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

HRID 1771679Notes

Reaction equation

HRID 1771679 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([Cl:10])[C:3]=1[N+:11]([O-])=O>CCOC(C)=O.[Pd]>[Cl:10][C:4]1[C:5]([O:8][CH3:9])=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH2:11]

Participants

4

Reactant 1

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

Product 1

HCID 205138882,6-Dichloro-3-methoxyanilineYield 104.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3-dichloro-4-methoxy-2-nitro-benzene (550 mg, 2.5 mmol, 1.0 eq) in EtOAc (20 mL) was added Pd/C (10% Pd, 50 mg) and the reaction was stirred under a hydrogen atmosphere overnight. The catalyst was removed by filtration and the filtrate was evaporated in vacuo to give the title compound (500 mg, 100%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-54c145e838a04a48bf8ebd85dace5a0b
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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