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

HRID 17726

Reaktionsgleichung

Reaktionsgleichung von HRID 17726
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7e638820e01040f09d961788b040414b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

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