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

HRID 1449573

Reaction equation

HRID 1449573 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 liltrate 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 liltrate 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-9f58e1ca23af46649bde517da2437f91
Source dataset
uspto-grants-1997_02
Patent number
US05599814

Linked notes

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