Nitrofen → 4-(2,4-Dichlorophenoxy)benzenamine

HRID 2237024

Reaction equation

HRID 2237024 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1.O.O.Cl[Sn]Cl>CO>[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 15787NitrofenHCID 61436Stannous chloride dihydrate

Product 1

HCID 269404-(2,4-Dichlorophenoxy)benzenamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The nitro intermediate (10 mmol) obtained above was dissolved in MeOH (20 mL), and treated with SnCl2.2H2O (50 mmol), according to General Procedure I. The reaction mixture was heated under reflux until completion, as indicated by TLC or HPLC. The solvent was removed in vacuuo and the residue was treated with 4.0 N aqueous NaOH to pH ˜8. The residue was extracted with EtOAc (2×50 mL), washed with 1.0 N aqueous NaOH (50 mL), brine (50 mL) and dried over sodium sulfate. The solvent was removed in vacuuo to afford the desired 4-(2,4-dichloro-phenoxy)aniline, which was used directly for further transformation without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux until completion
  3. customThe solvent was removed in vacuuo
  4. additionthe residue was treated with 4.0 N aqueous NaOH to pH ˜8
  5. extractionThe residue was extracted with EtOAc (2×50 mL)
  6. washwashed with 1.0 N aqueous NaOH (50 mL), brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-1c20915ecc344134be57b543f85d7785
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Linked notes

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