4-Aminophenol → HCID 59326808、化合物

HRID 410176

反応式

HRID 410176 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 59326808HCID 59326808、化合物

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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 RediSep® 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).

後処理

  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 RediSep® pre-packed silica gel column (120 g)
  8. washeluting with a gradient of 0% to 30% EtOAc in hexane

出典と根拠

ORDレコード
ord-8e3643de866e4aaab94d37818fd64280
出典データセット
uspto-grants-2014_06
特許番号
US08759532B2

関連ノート

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