Sodium Hydroxide → 4-Chloro-3-methoxyaniline

HRID 730100Notes

Reaction equation

HRID 730100 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

HCID 14798Sodium HydroxideHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 131036924-Chloro-3-methoxyaniline

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

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. Yield: 4.0 g, 79.36%.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted by ethyl acetate
  3. washwashed with water
  4. dry with materialbrine and dried over Na2SO4

Sources & evidence

ORD record
ord-1cd76f2ef0c743f9b9a3c993077e9756
Source dataset
uspto-grants-2009_09
Patent number
US07582661B2

Reaction notes

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