Stannous chloride dihydrate → 4-(4-Chloro-2-cyclohexylphenoxy)aniline

HRID 2237047Notes

Reaction equation

HRID 2237047 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)=[C:4]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:3]=1.O.O.Cl[Sn]Cl>CO>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[C:4]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:3]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 669774044-(4-Chloro-2-cyclohexylphenoxy)-1-nitrobenzene

Product 1

HCID 686845334-(4-Chloro-2-cyclohexylphenoxy)aniline

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, brine and dried over sodium sulfate. The solvent was removed in vacuuo to afford the desired 4-(4-chloro-2-cyclohexylphenoxy) 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, brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-54fcac7766284c11bdc8a6891aa33578
Source dataset
uspto-grants-2010_05
Patent number
US07714013B2

Reaction notes

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