Sodium Hydroxide → 3,5-Dichloro-4-methoxyaniline

HRID 3125

Reaction equation

HRID 3125 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][CH3:13].O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][CH3:13])[NH2:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 3097161,3-Dichloro-2-methoxy-5-nitrobenzene

Product 1

HCID 131786513,5-Dichloro-4-methoxyanilineYield 83.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2,6-dichloro-4-nitroanisole (4.6 g, 21 mM) and tin(II) dichloride dihydrate (23.4 g, 104 mM) in ethanol (72 mL) was refluxed for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice water which was then treated with 2N sodium hydroxide until the solution became basic. The resulting mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate. The combined ethyl acetate extracts were dried (MgSO4), filtered and concentrated to obtain (3.33 g, 83.7%) the title compound as a yellow-brown solid, mp 80°-81° C.; MS(CI): 192 (M+H).

Workup

  1. temperaturewas refluxed for 3 hr
  2. filtrationThe resulting mixture was filtered through diatomaceous earth
  3. extractionthe filtrate was extracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d1949a80f5a34ab9a1a505ee7b40c299
Source dataset
uspto-grants-1998_03
Patent number
US05733910

Linked notes

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