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

HRID 17726

반응식

HRID 17726 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7e638820e01040f09d961788b040414b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737285B2

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