4-Aminophenol → 4-[(3-methyl-2-pyridinyl)oxy]Benzenamine

HRID 1880043노트

반응식

HRID 1880043 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].F[C:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=1>CS(C)=O.CCOC(C)=O>[CH3:22][C:21]1[C:16]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)=[N:17][CH:18]=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 2427222-Fluoro-3-methylpyridine

생성물 1

HCID 593268084-[(3-methyl-2-pyridinyl)oxy]Benzenamine

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of 4-aminophenol (0.87 g, 8.0 mmol) in DMSO (12 mL) was added cesium carbonate (3.1 g, 9.6 mmol) and 2-fluoro-3-picoline (0.89 g, 8.0 mmol). The resulting mixture was heated to 80° C. for 16 h. After cooling to RT, the reaction mixture was diluted with EtOAc and washed with water and brine several times to remove DMSO. The aqueous layer was back extracted with EtOAc and the combined organic layer was dried (Na2SO4) and concentrated. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 0% to 30% EtOAc in hexane, to provide 4-(3-methylpyridin-2-yloxy)benzenamine as tan solid. MS (ESI, pos. ion) m/z: 201.2 (M+1).

후처리

  1. temperatureAfter cooling to RT
  2. washwashed with water and brine several times
  3. customto remove DMSO
  4. extractionThe aqueous layer was back extracted with EtOAc
  5. dry with materialthe combined organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (120 g)
  8. washeluting with a gradient of 0% to 30% EtOAc in hexane

출처 및 근거

ORD 기록
ord-88f79bfd94884830bca9d0a2d87159c5
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318718B2

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