1,4-Dioxane → 5-Chloro-4-methoxy-2-nitroaniline

HRID 2415666Notes

Reaction equation

HRID 2415666 reaction equation
[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH:8]C(=O)C)[CH:7]=1.O1CCOCC1>Cl>[Cl:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:7]=1)[NH2:8]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 27806535'-Chloro-4'-methoxy-2'-nitroacetanilide

Product 1

HCID 101043255-Chloro-4-methoxy-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(5-chloro-4-methoxy-2-nitrophenyl)-acetamide (2 g, 8.2 mmol) in 5N HCl (20 mL) is added 1,4-dioxane (10 mL), and the mixture is stirred at 60° C. for 1.5 hours. The reaction mixture is concentrated and partitioned between EtOAc/2 N NaOH. The aqueous layers are washed with EtOAc (3×), brine, dried (MgSO4), adsorbed onto silica gel, and chromatographed (70% EtOAc/hexanes) to provide an orange powder.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompartitioned between EtOAc/2 N NaOH
  3. washThe aqueous layers are washed with EtOAc (3×), brine
  4. dry with materialdried (MgSO4)
  5. customchromatographed (70% EtOAc/hexanes)
  6. customto provide an orange powder

Sources & evidence

ORD record
ord-31c0c745e0bb43f2af09e8df199a28e5
Source dataset
uspto-grants-2004_11
Patent number
US06821962B2

Reaction notes

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