Sodium Hydroxide → 4-Chloro-3-methoxyaniline
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].[OH-].[Na+]>CO.Cl>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:2]=1[Cl:1])[NH2:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
2-Chloro-5-nitro anisole (6.0 g, 0.032 mol) in MeOH (45 ml) was added slowly to stannous chloride (15.1 g, 0.08 mol) in conc. HCl (110 ml) at 40° C. and the temperature was slowly raised to 50° C. Stirring was continued for 2 h. After cooling to RT, the reaction mixture was basified with 50% NaOH solution, extracted by ethyl acetate, washed with water, then brine and dried over Na2SO4. 3-Methoxy-4-chloroaniline was obtained upon concentration and was purified further by column chromatography.
Workup
- temperatureAfter cooling to RT
- extractionextracted by ethyl acetate
- washwashed with water
- dry with materialbrine and dried over Na2SO4
Sources & evidence
- ORD record
- ord-e7a1884c2443436e84f576c317dc7d0d
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07420055B2
Reaction notes
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