Stannous Chloride → 2-Benzyloxy-6-methylaniline

HRID 660828

반응식

HRID 660828 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 33441871-Benzyloxy-3-methyl-2-nitrobenzene

생성물 1

HCID 27629472-Benzyloxy-6-methylaniline

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 1-benzyloxy-3-methyl-2-nitrobenzene (5.0 g, 20.6 mmol) in EtOAc (150 mL) is added SnCl2 (23.2 g, 103 mmol) and the suspension is heated at 80° C. overnight. The suspension is filtered and the filtrate washed with sat. NaHCO3 and extracted with EtOAc. The combined organic layers are washed with water, brine, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1) to give the title compound as a yellow oil.

후처리

  1. filtrationThe suspension is filtered
  2. washthe filtrate washed with sat. NaHCO3
  3. extractionextracted with EtOAc
  4. washThe combined organic layers are washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1)

출처 및 근거

ORD 기록
ord-497302fff055418384eab6c259e66d60
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084448B2

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