2-Chloro-5-nitroanisole → 4-Chloro-3-methoxyaniline

HRID 1593399Notes

Reaction equation

HRID 1593399 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[O:11][CH3:12]>CO.C1COCC1.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 1

HCID 705192-Chloro-5-nitroanisole

Product 1

HCID 131036924-Chloro-3-methoxyanilineYield 92.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 36 g of 2-chloro-5-nitroanisole and Raney® nickel in 150 ml of MeOH and 200 ml of THF is hydrogenated in Par apparatus for 4 hours, at 35° C. and at a pressure of 1.3 bar. The catalyst is filtered off on Celite® and the filtrate is concentrated under vacuum. 28 g of the expected product are obtained, and are used without further purification.

Workup

  1. filtrationThe catalyst is filtered off on Celite®
  2. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-a14f2cd4d5374279ac1e8d3d79d7bb03
Source dataset
uspto-grants-2007_11
Patent number
US07297692B2

Reaction notes

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