4-Chloro-2-nitroanisole → 5-Chloro-2-methoxyaniline
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
Product 1
Reagents, catalysts & solvents 1
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
- additionare added
- customis hydrogenated at atmospheric pressure and at room temperature
- customThe catalyst is separated
- washwashed with two portions of 20 ml of boiling ethanol
- concentrationThe alcoholic solution is concentrated under reduced pressure
- customthe 2-amino-4-chloroanisole crystallizes
Sources & evidence
- ORD record
- ord-8d2027cedc054e0d925f8ce20ae21344
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04211776
Reaction notes
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