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

HRID 2057571

Reaction equation

HRID 2057571 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-8d2027cedc054e0d925f8ce20ae21344
Source dataset
uspto-grants-1980_07
Patent number
US04211776

Linked notes

Loading…