Sodium Hydroxide → 4-Chloro-3-methoxyaniline

HRID 29508

Reaction equation

HRID 29508 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.

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-e7a1884c2443436e84f576c317dc7d0d
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Linked notes

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