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

HRID 2163200

Reaction equation

HRID 2163200 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1>[Ni]>[NH2:10][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

3

Reactant 1

HCID 666314-Chloro-2-nitroanisole

Product 1

HCID 667635-Chloro-2-methoxyaniline

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

0.037 mol (7 g) of 4-chloro-2-nitroanisole is dissolved in 100 ml of absolute alcohol and 3 g of nickel prepared by the RANEY process are added. The solution is hydrogenated at atmospheric pressure and at room temperature while stirring. The catalyst is separated and then washed with two portions of 20 ml of boiling ethanol. The alcoholic solution is concentrated under reduced pressure; the 2-amino-4-chloroanisole crystallizes.

Workup

  1. additionare added
  2. customis hydrogenated at atmospheric pressure and at room temperature
  3. customThe catalyst is separated
  4. washwashed with two portions of 20 ml of boiling ethanol
  5. concentrationThe alcoholic solution is concentrated under reduced pressure
  6. customthe 2-amino-4-chloroanisole crystallizes

Sources & evidence

ORD record
ord-c028b86f410243dba402322e62916b94
Source dataset
uspto-grants-1979_01
Patent number
US04132786

Linked notes

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